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Method for separating neogambogic acid and gambogic acid by medium and low pressure gradient silica gel dry column chromatography and method for preparing N-aryl garcinamide

A technology for separation of aryl gambogic amides and column chromatography, which is applied in organic chemistry and other fields, can solve the problems of limited separation technology popularization and high equipment cost, and achieve the effects of reducing three wastes, simple method and ensuring stability

Active Publication Date: 2019-11-12
JINING MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the high-speed countercurrent chromatography method, the price of each chromatograph is 500,000-600,000 RMB, and the equipment cost is high, which limits the popularization of this separation technology.
In addition, there is no literature report on the preparation of N-aryl gambogic amide so far, so it is urgent to find the residual GNA and GA etc. Component separation and GA aromatic amidation method

Method used

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  • Method for separating neogambogic acid and gambogic acid by medium and low pressure gradient silica gel dry column chromatography and method for preparing N-aryl garcinamide
  • Method for separating neogambogic acid and gambogic acid by medium and low pressure gradient silica gel dry column chromatography and method for preparing N-aryl garcinamide
  • Method for separating neogambogic acid and gambogic acid by medium and low pressure gradient silica gel dry column chromatography and method for preparing N-aryl garcinamide

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] The present invention passes figure 1 The separation device shown (the chromatographic column is equipped with silica gel H) selects dichloroethane-ethanol-triethylamine system as the eluent for one-time medium and low pressure gradient silica gel H dry column chromatography, which can be filtered out from the garcinia extract High-purity GA and GNA were isolated from the mother liquor of gambogic acid pyridinium salt.

[0050] The specific process steps are as follows:

[0051] (1) in such as figure 1 The chromatographic column with a piston at the bottom and a sand-permeable plate at the upper end is sequentially filled with silica gel H activated at 110°C for 2 hours [silica gel height: inner diameter>8:1, and the weight ratio of the sample to be separated (60-90): 1] After mixing the sample with coarse silica gel and 2-3mm fine sand layer, install a constant pressure dropping funnel with a piston and eluent, and a water pump for pumping;

[0052] (2) Shut down th...

Embodiment 2

[0060] EDCI.HCl, DMAP jointly catalyze the method for preparing N-aryl gambogic amide by reacting gambogic acid and arylamine, comprising the following steps:

[0061] (1) GA (initial concentration of 4.9mmol / L), 1-ethyl-3-(N,N-dimethylamino) propylcarbodiimide hydrochloride (EDCI.HCl, 1.1equiv., 5.5mmol / L initial concentration), 4-(N,N-dimethyl)pyridine (DMAP, 0.2equiv.,, 0.9mmol / L initial concentration) and dichloromethane (DCM) stirred at room temperature for 15min, then added 4- Chloro-3-trifluoromethylaniline (1.1 equiv., initial concentration of 4.8 mmol / L) in dichloromethane. Stirring was continued at room temperature for 11 h until the gambogic acid spots in the reaction solution were detected by silica gel TLC (developing agent: dichloromethane-ethanol-triethylamine v / v 80:0.1:3) completely disappeared;

[0062] (2) After adding water to quench the reaction, the organic layer was separated, washed with water (4 mL×2), and the organic phase was separated and dried ov...

Embodiment 3

[0064] EDCI.HCl, DMAP jointly catalyze the method for preparing N-aryl gambogic amide by reacting gambogic acid and arylamine, comprising the following steps:

[0065] (1) GA (initial concentration of 4.9mmol / L), 1-ethyl-3-(N,N-dimethylamino) propylcarbodiimide hydrochloride (EDCI.HCl, 1.1equiv., 5.5mmol / L initial concentration), 4-(N,N-dimethyl)pyridine (DMAP, 0.2equiv., 0.9mmol / L initial concentration) and dichloromethane (DCM) stirred at room temperature for 15min, then added 3-( 6-Chloropyridyl)amine (1.1 equiv., initial concentration of 4.8 mmol / L) in dichloromethane. Stirring was continued at room temperature for 12 hours until the GA spots in the reaction solution were detected by silica gel TLC (developing solvent: dichloromethane-ethanol-triethylamine v / v 80:0.1:3) completely disappeared;

[0066] (2) After adding water to quench the reaction, the organic layer was separated, washed with water (4 mL×2), and the organic phase was separated and dried over anhydrous ma...

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Abstract

The invention relates to a method for separating neogambogic acid (GNA) and gambogic acid (GA) by medium and low pressure gradient silica gel dry column chromatography and a method for preparing N-aryl garcinamide. The separation method comprises the following steps: silica gel H is used as a stationary phase, a selected eluent is utilized, treatment is performed by the medium and low pressure gradient silica gel dry column chromatography, and therefore the GA sample with purity of 90% and the GNA sample with purity of 93%can be separated in a low-cost, simple, convenient and larger-scale manner. The preparation method comprises the following steps: at room temperature under stirring, 1-ethyl-3-(3-N,N-dimethylaminopropyl)carbodiimide hydrochloride(or dicyclohexylcarbodiimide) and 4-(N,N-dimethylamino)pyridine is used to catalyze an amidation reaction of the gambogic acid and a substituted arylamine; and the crude product is treated by medium-pressure silica gel dry column chromatography using silica gel H as a stationary phase, and therefore the high-purity N-aryl garcinamide sample can be prepared in a low-cost, simple, convenient and larger-scale manner.

Description

technical field [0001] Extraction, separation and characterization of biologically active small molecules from natural products is one of the main ways to obtain lead compounds in the development of new drugs. The invention relates to a new method for separating new gambogic acid and gambogic acid and preparing N-aryl gambogic amide by medium and low pressure gradient silica gel dry column chromatography, which respectively belong to the technical fields of natural product separation and drug synthesis. Background technique [0002] Gambogic acid (GA), the active ingredient in the traditional Chinese medicine garcinia cambogia, has obvious inhibitory effects on the proliferation of tumor cell lines such as liver cancer, lung cancer, gastric cancer, nasal cancer and pancreatic cancer. Under the premise of hardly affecting normal hematopoietic cells and leukocytes, GA can selectively kill cancer cells through mechanisms such as inhibiting cell proliferation, arresting cell cyc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20C07D493/10
CPCC07D493/10C07D493/20
Inventor 周采菊张群郭道通张硕张艺雯杜俊郭永恩
Owner JINING MEDICAL UNIV
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