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Application of magnolol glucoside to preparing central nervous system disease treating drugs

A technology of central nervous system and honokiol, applied in the field of medicine

Active Publication Date: 2018-06-12
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, the prior art has no magnolol-4-O-β-D-glucopyranoside (1) and its pharmaceutical composition as a melatonin receptor agonist, and the treatment or prevention of melatonin receptor-related Application reports of central nervous system diseases

Method used

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  • Application of magnolol glucoside to preparing central nervous system disease treating drugs
  • Application of magnolol glucoside to preparing central nervous system disease treating drugs
  • Application of magnolol glucoside to preparing central nervous system disease treating drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Preparation of Compound 1:

[0026] ①Take 1.56g (4mmol) of 1,2,3,4,6-pentaacetylated glucose and dissolve it in 10.0mL of dichloromethane; add 1.72mL of acetic acid solution containing 30% HBr in an ice bath (10mmol), reacted for about 4 hours; after TLC detected that the reaction was complete, add 40mL dichloromethane to dilute, wash three times with 150mL ultrapure water (50mL each time), and the organic layer was washed with anhydrous Na 2 SO 4 Drying; the organic layer was recovered under reduced pressure to obtain the product 1-α-Br-2,3,4,6-tetraacetylated glucose (1.62 g), with a yield greater than 99%. ②Weigh 0.5mmol (133mg) of magnolol and dissolve it in 10mL of 0.8N NaOH aqueous solution; weigh 0.5mmol (206mg) of 1-α-Br-2,3,4,6-tetraacetylated glucose and 0.05mmol of tetrabutylammonium bromide (catalyst, TBAB), fully dissolved in 5.0mL of chloroform; the dissolved chloroform solution was added dropwise in the magnolol solution, and constantly stirred, reacted...

Embodiment 2

[0039] Compound 1 on melatonin receptor MT 1 and MT 2 Agonistic activity of the receptor.

[0040] 1 Materials and methods

[0041] 1.1 Materials:

[0042] melatonin receptor MT 1 and MT 2 The cell lines used for agonistic activity screening correspond to human kidney epithelial cells HEK293-MT 1 and HEK293-MT 2 ; Cell culture medium (Dulbecco's Modified Eagle Medium, DMEM) containing 10% fetal bovine serum; No-wash calcium flow kit.

[0043] 1.2 Instrument: CO 2 Constant temperature incubator Thermo Forma 3310 (USA); Inverted biological microscope XD-101 (Nanjing); Flexstation 3 Benchtop Multi-Mode Microplate Reader (Molecular Devices, Sunnyvale, California, USA).

[0044] 1.3 Experimental process

[0045] Coat the 96-well black-walled transparent-bottom cell culture plate with the substrate BD Matrigel, put it in a constant temperature incubator at 37°C for 1 hour, absorb the supernatant, and dilute it with 4×10 4 Density per well, the corresponding HEK293 cells we...

Embodiment 3

[0051] Effects of compound 1 on behavioral animal models related to depression

[0052] 1 Materials and methods

[0053] 1.1 Materials: Fluoxetine hydrochloride (Sarn Chemical Technology Co., Ltd., Shanghai, China); agomelatine (Sarn Chemical Technology Co., Ltd., Shanghai, China). Sodium carboxymethylcellulose 800-1200 (Sinopharm Group, Shanghai, China). Kunming mice 18-20 g (Beijing Huafukang Biotechnology Co., Ltd., Beijing, China), license number: SCXK (Beijing) 2014-0004.

[0054] 1.2 Method: The mice were divided into random groups, 10 in each group, and measured after 5 consecutive days of administration. Spontaneous activities mice were put into the bottom center of a black dark box with a length, width and height of 24x24x40cm, and the ANY-maze automatic collection system (Anymaze, Stoelting Co., Wooddale, USA) was used to record for 6 minutes, and the time was 5 minutes and 30 seconds after analysis. The number of crossings and the total distance traveled by the m...

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Abstract

The invention provides application of magnolo-4-O-beta-D-glucopyranoside (1) shown as the structural formula (I) or medicinal salts and pharmaceutical compositions thereof to preparing melatonin receptor agonists as well as preparing drugs for treating or preventing central nervous system diseases correlated with melatonin receptors. The magnolo-4-O-beta-D-glucopyranoside (1) is prepared through achemical synthesis method.

Description

Technical field: [0001] The invention belongs to the technical field of medicines. Specifically, it relates to a phenolic compound magnolol-4-O-β-D-glucopyranoside (1) or a pharmaceutically acceptable salt thereof and a pharmaceutical composition thereof, which are used as a melatonin receptor agonist, and Its application in the preparation of medicines for treating or preventing central nervous system diseases related to melatonin receptors. Background technique [0002] Melatonin (N-acetyl-5-methoxytryptamine, Melatonin) is an amine hormone mainly produced by the pineal gland in the human body. It was first isolated from bovine pineal tissue by Lerner et al. in 1958. The production of melatonin is mainly through the conversion of L-tryptophan into 5-hydroxytryptamine in pineal cells, and then generates N-acetyl 5-hydroxytryptamine under the action of N-acetyltransferase (AA-NAT), and finally in 5-hydroxytryptamine. Melatonin is produced by the enzyme oxindoleoxymethyltr...

Claims

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Application Information

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IPC IPC(8): A61K31/7034C07H15/203C07H1/00C07H1/06A61P25/00A61P25/24
CPCA61K31/7034C07H1/00C07H1/06C07H15/203
Inventor 陈纪军杨通华耿长安马云保颜得秀黄晓燕张雪梅
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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