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Preparation of ginsenoside M1 n-butyrate and application of antidiabetic medicines of ginsenoside M1 n-butyrate

A technology of n-butyrate and ginsenoside, which is applied in the direction of pharmaceutical formulations, medical preparations containing active ingredients, metabolic diseases, etc., can solve problems such as anti-diabetic literature reports, and achieve less impurities, high yield, and substrate fully responsive effect

Inactive Publication Date: 2013-02-27
JILIN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The above-mentioned artificially synthesized products and their anti-diabetic literature reports were not found after searching

Method used

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  • Preparation of ginsenoside M1 n-butyrate and application of antidiabetic medicines of ginsenoside M1 n-butyrate
  • Preparation of ginsenoside M1 n-butyrate and application of antidiabetic medicines of ginsenoside M1 n-butyrate
  • Preparation of ginsenoside M1 n-butyrate and application of antidiabetic medicines of ginsenoside M1 n-butyrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] a) Dissolve 1.0g of M1 in 250mL THF, fully dissolve, add 10mL of 10mg / mL DMAP solution in THF to the reaction solution, incubate for 3-5min, then slowly add 500 mg of n-Butyric anhydride to the system, react 0.1-1h; after the reaction is completed, the reaction solution is concentrated, and the dry matter is dissolved with ethyl acetate, then washed with water and saturated brine in sequence, and the ethyl acetate is recovered under reduced pressure to obtain a dry matter.

[0037] b) The dry matter was dissolved in a small amount of methanol, filtered, and subjected to silica gel column chromatography, eluting with chloroform-methanol (30:1-5:1), followed by TLC; the target products were combined and recovered under reduced pressure to obtain 0.723 g of dry matter. That is, ginsenoside M1 monoester n-BM1, in which fatty acyl is C 4 The fatty acyl group (the fatty acyl group is connected to the C’6 position of the sugar chain of the C-20 glucose group), see HPLC figur...

Embodiment 2

[0039] a) Weigh 500mg of ginsenoside M1, dissolve it in 150mL THF, fully dissolve, add 5mL of 5mg / mL DMAP solution in THF to the reaction solution, incubate for 3-5min, then slowly add 250 mg of n-Butyric anhydride into the system , react for 0.1-1h; after the reaction, concentrate the reaction solution, dissolve the dry matter with ethyl acetate, then sequentially water, saturated brine, and recover the ethyl acetate under reduced pressure to obtain dry matter.

[0040] b) The dry matter was dissolved in methanol, filtered, and subjected to silica gel column chromatography, eluting with chloroform-methanol (30:1-5:1), followed by TLC; the target products were combined and recovered under reduced pressure to obtain 0.35 g of dry matter. That is, ginsenoside M1 monoester n-BM1, in which fatty acyl is C 4 The fatty acyl group (the fatty acyl group is connected to the C’6 position of the sugar chain of the C-20 glucose group), see HPLC figure 1 .

Embodiment 3

[0042]a) Weigh 750mg of ginsenoside M1, dissolve it in 200mL THF, fully dissolve, add 8mL of 7.5mg / mL DMAP solution in THF to the reaction solution, incubate for 3-5min, then slowly add n-Butyric anhydride 400 into the system mg, reacted for 0.1-1h; after the reaction was completed, the reaction solution was concentrated, and the dry matter was dissolved with ethyl acetate, then washed with water and saturated brine in sequence, and the ethyl acetate was recovered under reduced pressure to obtain a dry matter.

[0043] b) The dry matter was dissolved in methanol, filtered, and subjected to silica gel column chromatography, eluting with chloroform-methanol (30:1-5:1), followed by thin-layer chromatography; the target products were combined and recovered under reduced pressure to obtain 0.5 g of dry matter. That is, ginsenoside M1 monoester n-BM1, in which fatty acyl is C 4 The fatty acyl group (the fatty acyl group is connected to the C’6 position of the sugar chain of the C-20...

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Abstract

The invention provides ginsenoside M1 n-butyrate which is a new compound with a molecular formula of C40H69O9. The molecular weight of the ginsenoside M1 n-butyrate is 692. The invention further discloses a preparation method of the compound and application of antidiabetic medicines of the compound. The ginsenoside M1 n-butyrate can resist to physiological activity of diabetes mellitus and can be used for preventing and treating the diabetes mellitus and conducting assistant treating the diabetes mellitus.

Description

technical field [0001] The invention relates to ginsenoside M1 n-butyrate (hereinafter referred to as n-BM1) compounds, and discloses the molecular structure, synthesis method and pharmaceutical composition with the compound as the active ingredient, belonging to the semi-synthesis of chemical components of traditional Chinese medicine technology. Background technique [0002] The compound prepared by the present invention is a fatty acid ester substance of ginsenoside M1 (hereinafter referred to as: M1), and its lead compound is ginsenoside M1, also known as Compound K. In 1972, Japanese scholar Yasioka used soil bacteria to degrade diol-type ginsenosides. Ginsenoside M1 was discovered for the first time, and it was deduced that M1 is a panaxadiol group saponin (Rb 1 ,Rb 2 , Rc, Rd, etc.) The secondary saponin that removes one or several glycosidic groups at the C-3 position of the mother nucleus and the C-20 glucose group. [0003] M1 has good physiological and pharmaco...

Claims

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Application Information

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IPC IPC(8): C07J17/00A61K31/7032A61P3/10
Inventor 郑毅男徐玉林刘文丛李伟李慧萍李永娟
Owner JILIN AGRICULTURAL UNIV
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