Preparation method and medicinal application of ginsenoside Rh2 aliphatic ester compound

A technology of ginsenosides and fatty acid esters, applied in steroids, pharmaceutical formulations, organic chemistry, etc., can solve the problems of no artificial synthesis products reported in literature, and achieve the effect of less impurities, high yield and complete reaction

Inactive Publication Date: 2012-07-25
JILIN AGRICULTURAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] No literature reports on the above artificia

Method used

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  • Preparation method and medicinal application of ginsenoside Rh2 aliphatic ester compound
  • Preparation method and medicinal application of ginsenoside Rh2 aliphatic ester compound
  • Preparation method and medicinal application of ginsenoside Rh2 aliphatic ester compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 2

[0050] a) Ginsenoside secondary glycoside Rh 2 , the sample was purified by conventional silica gel column chromatography and recrystallization to obtain pure product.

[0051] b) take Rh 2 5g was dissolved in 100mL chloroform and set aside. Measure octanoyl chloride 4.1g, triethylamine 4.5g, put in 100mL chloroform solution, react for 15-30min, then slowly add Rh 2 chloroform solution. After 12-48 hours of reaction, chloroform was recovered under reduced pressure to obtain dry matter.

[0052] c) The dry matter was dissolved in methanol, filtered, ODS column chromatography, eluting with methanol and water (80%-100%), and the combined target product was detected by thin-layer chromatography, and recovered under reduced pressure to obtain 3.27 g of dry matter. That is, ginsenoside secondary glycoside fatty acid ester derivatives, wherein the fatty acyl group is C 8 The fatty acyl group (the fatty acyl group is connected at the C-12 position of the mother nucleus).

Embodiment 3

[0054] a) Ginsenoside secondary glycoside Rh 2 , the sample was purified by conventional silica gel column chromatography and recrystallization to obtain pure product.

[0055] b) take Rh 2 3.0g was dissolved in 100mL chloroform and set aside. Measure 3.2g of fatty acid chloride and 3.5g of potassium carbonate, place in 100mL chloroform solution, suspend for 15min, and then slowly add Rh 2 chloroform solution. After reacting for 12-24h, chloroform was recovered under reduced pressure to obtain dry matter.

[0056] c) is the same as c) in the example (2).

[0057] 4.4. Embodiment 4

[0058] a) Ginsenoside secondary glycoside Rh 2 , the sample was purified by conventional silica gel column chromatography and recrystallization to obtain pure product.

[0059] b) Accurately weigh ginsenoside Rh 2 50.0mg, synthesize C-Rh with the method in example 1 2 , The obtained dry matter was fixed to volume in a 50 ml volumetric flask with 50 ml of chromatographic methanol, and the...

experiment example 7

[0091] 4.7 Experimental Example 7 Compound C-Rh 2 Anti-HepaG2 Human Tumor Cell Effect in Vitro

[0092] 4.7.1 Experimental materials and methods

[0093] Experimental materials: Cell lines: HepaG2 human tumor cells are cell lines preserved in the pharmacology laboratory of Bethune School of Medicine, Jilin University. Synthetic product C-Rh 2 .

[0094] method:

[0095] 1. HepaG2 cells were revived, cultured in 1640 medium containing 10% fetal bovine serum for 24 hours, and then cultured in serum-free 1640 medium for 24 hours.

[0096] 2. Select the HepaG2 cells treated above (in the logarithmic growth phase) and inoculate them in a 96-well culture plate. The experimental group is replaced with a new medium containing the samples to be tested at different concentrations, and the control group is replaced with a medium containing an equal volume of solvent. , set 3 parallel wells for each group, and set up a control well for the drug solution, at 37°C in 5% CO 2 Culture ...

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PUM

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Abstract

The invention discloses two ginsenoside Rh2 aliphatic ester compounds. The compounds have the following structural formula described in the specification. In the formula, R is a C4-C22 fatty acid acyl. The invention also provides the chemical synthesis and enzymatic synthesis methods of the ginsenoside Rh2 aliphatic ester compounds, a pharmaceutical composition which takes the compounds as active ingredients and an application of the compounds and the pharmaceutical composition in preparation of an anticancer drug.

Description

1 technical field [0001] The present invention relates to ginsenoside Rh 2 Fatty acid ester compounds, and disclose the molecular structure of the compound, synthesis method and pharmaceutical composition with the compound as the active ingredient, which belongs to the semi-synthesis technology of chemical components of traditional Chinese medicine. 2 background technology [0002] The compound involved in the present invention is ginsenoside Rh 2 fatty acid esters, its lead compound ginsenoside Rh 2 It was first isolated from red ginseng by Japanese scholars in 1983. It belongs to protopanaxadiol group saponins, and the 20th carbon atom shows chirality. Rh 2 Ginsenoside Rg 3 The secondary glycoside that removes a glycoside is Rg 3 The main metabolite in the body. Rg 3 Shenyi Capsules, a new anti-cancer drug that has been developed as a traditional Chinese medicine, has been successfully marketed, but pharmacokinetic studies have found that Rg 3 The oral bioavailabil...

Claims

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Application Information

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IPC IPC(8): C07J17/00C12P33/20A61K31/704A61P35/00
CPCY02P20/54
Inventor 郑毅男刘发贵张成中李伟
Owner JILIN AGRICULTURAL UNIV
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