Monoterpenyl bishydroxycoumarin compound, pharmaceutical composition, preparation method of monoterpenyl bishydroxycoumarin compound, and application of monoterpenyl bishydroxycoumarin compound and pharmaceutical composition

A technology of dicoumarins and compounds, applied in the field of natural medicinal chemistry, can solve problems such as unclear etiology

Active Publication Date: 2020-10-30
CHINA RESOURCES SANJIU MEDICAL & PHARMA
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The etiology o...

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  • Monoterpenyl bishydroxycoumarin compound, pharmaceutical composition, preparation method of monoterpenyl bishydroxycoumarin compound, and application of monoterpenyl bishydroxycoumarin compound and pharmaceutical composition
  • Monoterpenyl bishydroxycoumarin compound, pharmaceutical composition, preparation method of monoterpenyl bishydroxycoumarin compound, and application of monoterpenyl bishydroxycoumarin compound and pharmaceutical composition
  • Monoterpenyl bishydroxycoumarin compound, pharmaceutical composition, preparation method of monoterpenyl bishydroxycoumarin compound, and application of monoterpenyl bishydroxycoumarin compound and pharmaceutical composition

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experiment example 1

[0089] 1. Purpose of the experiment

[0090] The SH-SY5Y cell model induced by the modeling agent scopolamine was used to study the neuroprotective effect of the compound, as well as the influence of oxidative stress and inflammation, and investigate the anti-senile dementia effect of compounds 1-10 of the present invention.

[0091] 2. Experimental method

[0092] 1. Experimental materials

[0093] Preparation of the tested sample solution: the tested sample is the pure compound 1-10 isolated and refined in the following example 1, and the compound 1-10 is precisely weighed and dissolved in DMSO, and the compound 1-10 is prepared to contain the concentration of the compound 1-10 respectively. The mother solution is 30mM, where mM is mmol / L, and the mother solution of each compound is diluted with DMSO to obtain the following concentration gradient solution, 0.1nM, 1nM, 10nM, 100nM, where nM is nmol / L.

[0094] Preparation of positive control solution (donepezil solution...

Embodiment 1

[0121] The preparation of embodiment 1 compound 1-10

[0122] (1) Take the bitter stem of Trigemina, add 12 times of the weight of the stem of Trigemina, and add 70% ethanol aqueous solution for reflux extraction once, heat reflux time at 92°C for 2h, collect the ethanol extract; The volume ratio of 10 times the weight of the root is 70% ethanol aqueous solution for reflux extraction once, heat reflux time at 92 ° C for 2 hours, and collect the ethanol extract; the remaining medicinal residues are added to the volume ratio of 8 times the weight of the root of Trident bitter root to be 70% The ethanol aqueous solution was refluxed and extracted once, and the reflux time was 2 hours, and the ethanol extract was collected; the ethanol extracts were combined, concentrated under reduced pressure until no alcohol smell, and 4 kg of ethanol extract was obtained.

[0123] (2) After dissolving 4 kg of ethanol extract with distilled water, extract with sherwood oil, ethyl acetate, n-but...

Embodiment 2

[0127] The characterization of embodiment 2 racemate 1-5 and compound 1-10

[0128]

[0129] Racemate 1 is a white amorphous powder, and the HR-ESI-MS spectrum gives a quasi-molecular ion peak m / z 457.1649[M+H] + (calcd.for 457.1651), combined with 13 C NMR spectrum deduces that the molecular formula of compound 1 and compound 2 is C 28 h 24 o 6 . Ultraviolet spectrum (UV) shows characteristic absorption of coumarin (λ max 202nm, 246nm, 333nm); Infrared spectrum (IR) showed hydroxyl absorption (3647cm -1 ), carbonyl absorption (1716cm -1 ).

[0130] 1 In the H-NMR spectrum, a set of characteristic hydrogen signals of coumarin nuclei were observed in the low field region: δ H 6.10 (1H, d, J = 9.4Hz, H-3) and δ H 7.79 (1H, d, J = 9.4Hz, H-4); a set of E-configuration double bond proton signals: δ H 5.96(1H,d,J=16.4Hz,H-9') and δ H 6.71 (1H, d, J=16.4Hz, H-10′); in addition, there are two ene hydrogen proton signals in the low field region: δ H 5.30(1H,brs...

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Abstract

The invention relates to the field of natural pharmaceutical chemistry and specifically provides a monoterpenyl bishydroxycoumarin compound, a pharmaceutical composition, a preparation method of the monoterpenyl bishydroxycoumarin compound, and application of the monoterpenyl bishydroxycoumarin compound and the pharmaceutical composition. The monoterpenyl bishydroxycoumarin compound has a structure as shown in a formula (I) which is described in the specification. In the formula, R1 to R6 and X1 to X4 are as defined in the specification. The monoterpenyl bishydroxycoumarin compound provided bythe invention can protect nerve cells from damage by inhibiting the activity of acetylcholin esterase, and has anti-inflammatory and antioxidant effects. Therefore, the compound can be used for preparing medicines for preventing and treating nervous system degenerative diseases such as senile dementia (also called Alzheimer's disease), cholinergic neurodegenerative change, learning and memory ability decline and the like.

Description

technical field [0001] The invention relates to the field of natural medicinal chemistry, in particular to a monoterpene-based dicoumarin compound, a pharmaceutical composition and a preparation method and application thereof. Background technique [0002] Central nervous system degenerative disease is a kind of chronic and degenerative nervous system disease. There are no effective measures to control the progress of this kind of disease clinically. Patients will eventually lose their ability to live or even die. For example, Alzheimer's disease accounts for The cause of 60%-70% of dementia has now become one of the greatest threats to human health in the 21st century. The latest statistics show that there are about 40 million people over the age of 60 suffering from AD in the world, and there are 7.7 million new cases every year, so it has become an important public health problem in the world. However, the etiology of AD is still unclear. Therefore, it is urgent to find...

Claims

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Application Information

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IPC IPC(8): C07D311/16A61P25/28A61P25/00A61K31/37
CPCC07D311/16A61P25/28A61P25/00C07B2200/07
Inventor 张容容刘中秋章时杰刘晖晖韩正洲马庆魏伟锋许雷魏民张洪胜李明辉黄煜权谢文波曾烨张赟马鹏岗
Owner CHINA RESOURCES SANJIU MEDICAL & PHARMA
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