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Novel quinolone alkaloid in Evodia rutaecarpa, and preparation method, application and pharmaceutical composition of such quinolone alkaloid

A technology of quinolones and Evodia rutaecarpa, which is applied in the field of compound extraction and separation, can solve problems such as unclear mechanism of action, unstable curative effect, and complex components of traditional Chinese medicine, and achieve excellent neuroprotective effect

Inactive Publication Date: 2017-06-09
NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the composition of traditional Chinese medicine is complex, the active ingredients are not clear, the curative effect is unstable, and the mechanism of action is not clear, which seriously affects the clinical use and the entry of Chinese medicine into the international mainstream market. Drugs for the treatment of degenerative diseases are an urgent task for medical researchers for a long time to come

Method used

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  • Novel quinolone alkaloid in Evodia rutaecarpa, and preparation method, application and pharmaceutical composition of such quinolone alkaloid
  • Novel quinolone alkaloid in Evodia rutaecarpa, and preparation method, application and pharmaceutical composition of such quinolone alkaloid
  • Novel quinolone alkaloid in Evodia rutaecarpa, and preparation method, application and pharmaceutical composition of such quinolone alkaloid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: The preparation method of new quinolone alkaloid compound 1 in Evodia rutaecarpa comprises the following steps:

[0028] 10 kg of Evodia rutaecarpa medicinal materials were reflux extracted with 90% ethanol for 3 times, each time for 2 hours, and the combined extracts were concentrated under reduced pressure to obtain an extract (800 g). After the extract was dispersed in water, it was extracted several times with petroleum ether, chloroform, and n-butanol in sequence, and the solvents were respectively recovered under reduced pressure. 32, 200, 320 g of each extract were obtained sequentially. Chloroform extract 200g was crudely separated by silica gel (200-300 mesh, 3 kg) column chromatography, CHCl 3 / CH 3 COCH 3 (100:1→1:100) gradient elution, each fraction 2000 ml, a total of 167 fractions were collected, and then 167 fractions were combined by TLC to obtain 5 fractions Fr (1-5) ; Fr.3 (30 g) was subjected to open ODS column chromatography (MeOH:...

Embodiment 2

[0029] Example 2: Application of the new quinolone alkaloid compound 1 in Evodia rutaecarpa in the preparation of drugs for the prevention and / or treatment of neurodegenerative diseases. The neurodegenerative diseases are stroke, dementia, neuroinflammation, heavy metal poisoning, and nerve agent poisoning. The dementia is Alzheimer's disease or vascular dementia.

[0030] The physicochemical and spectral data of the new quinolone alkaloids of Evodia rutaecarpa are as follows:

[0031] Yellow oil, ESI-MS m / z 256 [M+H] + . 1 H-NMR (CDCl 3 , 500 MHz) and 13 C-NMR (CDCl 3 , 125 MHz) see the table below for data

[0032] Table 1 Compound 1 1 H and 13 C-NMR data (CDCl 3 , J in Hz)

[0033]

[0034] a The signals were overlapped.

[0035] Pharmacological experiment

[0036] Test materials 1. Test drug: monomer compound of the present invention. 2. Positive control drug: Edaravone, provided by China National Institutes for Food and Drug Control. Purity > 98% by HP...

experiment example 1

[0037] Experimental example 1: Effect of the compound of the present invention on the survival state of rat cerebral cortex neurons and its protective effect in the model of neuron apoptosis induced by sodium nitroprusside

[0038] In the study of the effect of the compound on the survival state of neurons, the primary cultured rat cortical neurons (DIV-9) were divided into a control group and an administration group (10 μM), n=6; In the study of the protective effect of the apoptosis model, the primary cultured rat cortical neurons (DIV-7) were divided into control group, sodium nitroprusside (350 μM) model group, sodium nitroprusside (350 μM) + ida Lavone (100 μM) administration group, sodium nitroprusside (350 μM) + compound (10 μM) administration group, n =6. After administration, the cells were placed in a cell incubator to continue culturing for 24 hours, and the cell viability was measured by MTT method (570 nm). Taking the absorbance of the control group as the standa...

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Abstract

The invention discloses a novel quinolone alkaloid compound 1 extracted from Evodia rutaecarpa, a preparation method of the novel quinolone alkaloid compound, a pharmaceutical composition containing the novel quinolone alkaloid compound and application thereof to neuroprotective drugs, in particular to drugs for treating the Alzheimer's disease. Pharmacological experiments show that neuroprotective activity is embodied in the novel quinolone alkaloid compound, in other words, the novel quinolone alkaloid compound has excellent neuroprotective activity in a sodium-nitroprusside-induced primary neuron damage model and a glutamate-induced primary neuron toxicity model.

Description

technical field [0001] The invention relates to the field of compound extraction and separation, in particular to new quinolone alkaloids in Evodia rutaecarpa and its preparation method, application and pharmaceutical composition. Background technique [0002] Evodia ( Evodia rutaecarpa (Juss.) Benth.), alias Wuyu, tea spicy, lacquer spicy, smelly spicy tree, Zuo Lichun Youzi, rice spicy and so on. It is usually divided into several varieties such as large flower Evodia, medium flower Evodia and small flower Evodia. Small trees or shrubs, 3-5 meters high, twigs dark purple, covered with gray-yellow or red rust-colored tomentose, or sparsely short-haired. Born in open forests or shrubs in mountains from flat to 1500 meters above sea level, more common in sunny slopes. There are small or large plantings in various places. After soaking and drying the tender fruit, it becomes the traditional Chinese medicine Evodia rutaecarpa, referred to as Evodia rutaecarpa for short. I...

Claims

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Application Information

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IPC IPC(8): C07D215/233A61K31/47A61P25/28A61P25/00
CPCC07D215/233
Inventor 庄鹏宇王晓霞陈金铭张丹阳林晓莹杨宇柯
Owner NORTH CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY
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