Gastrodin derivatives as well as preparation method and application thereof

A technology of gastrodin and derivatives, applied in the field of medicine, to achieve the effects of sedative and analgesic brain circulation, inhibition of nerve cell damage, and inhibition of activity

Active Publication Date: 2021-05-28
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Wu Hongbin et al disclosed the preparation and application of gastrodin derivative 4-(acetoxymethyl)phenyl glucopyranoside in CN200410056936 in 2004; Preparation and application of compounds; Song Liming et al. disclosed in CN201610435276 and CN201611017077 in 2016 a kind of anti-senile dementia of gastrodin aglycone and anti-nonalcoholic fatty liver of a kind of acetyl gastrodin and acetyl gastrodin derivatives; However, there is no public report on the combination of gastrodin and mannuronic acid for the improvement of central nervous system diseases or thrombotic diseases and metabolic syndrome

Method used

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  • Gastrodin derivatives as well as preparation method and application thereof
  • Gastrodin derivatives as well as preparation method and application thereof
  • Gastrodin derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, the preparation method of series compound A-G

[0034] In the process of preparing the A series derivatives, it is first necessary to prepare 1-bromo-2,3,4-acetyl-6-formylmannide, and 3-{3-methoxy-4-[(2-acetyloxy Base) benzoyloxy] phenyl} acrylic acid, which can be prepared according to the preparation methods well known to those skilled in the art, and there is no special limitation in this application.

[0035] (1) Using p-hydroxybenzaldehyde as raw material, in anhydrous dichloromethane, add 1-bromo-2,3,4 acetyl-6-formyl mannoate and boron trifluoride ethyl ether successively under nitrogen protection, room temperature After the reaction is completed, add saturated sodium bicarbonate solution, separate the organic phase, wash with saturated sodium bicarbonate and water, dry over anhydrous sodium sulfate, and obtain p-acyl mannide benzaldehyde through column chromatography, p-acyl mannide benzaldehyde Under the catalysis of NaBH4, the aldehyde group can...

Embodiment 2

[0072] Example 2. Protective effect of gastrodin-derived compounds on nerve cell damage induced by Aβ aggregates

[0073] Using the cell viability without adding Aβ1-42 as a negative control, observe the inhibitory effect of a series of compounds on the neurotoxicity induced by Aβ. The specific implementation steps are as follows: Inoculate PCl2 cells in MEM complete culture medium and place them in a 96-well plate After culturing in a constant temperature cell incubator for 24 hours, add the pre-aggregated Aβ protein oligomers. After 2 hours, add a series of compound solutions to each well with a concentration of 200ug / ml, and continue to incubate in the incubator for 24 hours. After the end, the cell viability was measured by MTT method. Three parallels were performed each time, and the experiment was repeated three times.

[0074] The results in Table 1 show that the gastrodin derivatives of the present invention have a better protective effect on nerve cells, and have a s...

Embodiment 3

[0077] Embodiment 3, series compound A-I to CoCl 2 Protective Effects of Induced Hypoxic Injury on Nerve Cells and Cardiomyocytes

[0078] without CoCl 2 The cell viability of the induced nerve cells PC12 and cardiomyocytes H9C2 was used as a negative control to observe the effect of a series of compounds on the induction of CoCl 2 The inhibition of hypoxic injury of nerve cells and cardiomyocytes, the specific implementation steps are as follows: inoculate PC12 and H9C2 cells in MEM or DMEM complete culture medium, place them in a 96-well plate for culture, put them in a constant temperature cell incubator and incubate for 24 Hours later, the pre-dissolved injury solution containing CoCl2 was added, and after 2 hours, a series of compound solutions were added to each well with a concentration of 200ug / ml, and the incubator continued to incubate for 48 hours. After the end, the cell viability was measured by MTT method. Three parallels were performed each time, and the expe...

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Abstract

The invention provides gastrodin derivatives as well as a preparation method and an application thereof. The gastrodin derivative with the novel structure, provided by the invention, can effectively protect nerve cells from being damaged by A beta aggregates; the CoCl2 hypoxia injury is avoided; the damage of hydrogen peroxide is avoided; meanwhile, the effects of calming, easing pain and improving brain circulation on mice are achieved; meanwhile, the effect of inhibiting platelet aggregation can also be achieved; and the symptom of mouse metabolic syndrome caused by feeding with high-fat feed can also be obviously improved. Therefore, the gastrodin derivative disclosed by the invention can be used for effectively preventing and treating central nervous system diseases and/or thrombotic diseases and/or metabolic syndromes; more importantly, the effect of the gastrodin derivative with the novel structure is obviously superior to that of gastrodin with a single dosage; the synergistic interaction effect is achieved; the invention widens the new application of the novel gastrodin derivative; and the method has huge economic and social values.

Description

technical field [0001] The invention belongs to the technical field of medicine, and specifically relates to a class of gastrodin derivatives, a preparation method and application thereof. Background technique [0002] Gastrodin, also known as 4-hydroxymethylphenyl-beta-D-glucopyranoside, is the dry root extract of the orchid plant Gastrodia elata, which has good sedative and hypnotic effects, and is effective for neurasthenia, Insomnia, headache symptoms have a relieving effect. It is clinically used to treat vertebral-basilar artery insufficiency, vestibular neuronitis and vertigo. Gastrodin injection can expand cerebral blood vessels, improve the ability of brain cells to resist hypoxia, increase cerebral blood flow, and reduce cerebral vascular resistance. At the same time, gastrodin can improve the insufficient blood supply of the anterior inferior cerebellar artery, posterior inferior cerebellar artery, labyrinthine artery and inner ear, protect nerve cells, and prom...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H15/203C07H1/00A61K31/7034A61P7/02A61P3/00A61P25/20A61P25/28A61P25/16A61P25/04A61P3/10A61P3/06A61P1/16
CPCC07H15/203C07H1/00A61P7/02A61P3/00A61P25/20A61P25/28A61P25/16A61P25/04A61P3/10A61P3/06A61P1/16Y02P20/55
Inventor 郝杰杰江涛王东平于广利管华诗
Owner OCEAN UNIV OF CHINA
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