Peotopanaxadiol ginsenoside derivative and preparation method and application thereof

A ginsenoside and diol type technology, applied in the field of medicine, can solve the problems of low activity, lack of practical application value, cytotoxicity, etc., and achieve the effects of low cytotoxicity, lowering the level of low-density lipoprotein cholesterol, and good anti-inflammatory effect.

Active Publication Date: 2017-05-10
ARMY MEDICAL UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are more than 40 kinds of ginsenoside monomers with a clear structure. Studies have found that diol-type ginsenosides have a certain preventive effect on atherosclerosis. Further mechanism studies have shown that their pharmacological effects include regulating blood lipids, reducing inflammation, and reducing smooth muscle. Proliferation, etc., but its activity is low, and it has certain cytotoxicity, lack of practical application value

Method used

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  • Peotopanaxadiol ginsenoside derivative and preparation method and application thereof
  • Peotopanaxadiol ginsenoside derivative and preparation method and application thereof
  • Peotopanaxadiol ginsenoside derivative and preparation method and application thereof

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preparation example Construction

[0048]The present invention provides the preparation method of diol type ginsenoside derivative described in above-mentioned technical scheme, comprises the following steps:

[0049] (1) Carrying out a nucleophilic substitution reaction between the parent compound and the acid anhydride in the presence of an alkaline reagent to obtain the first intermediate product;

[0050] (2) performing an oxidation reaction on the first intermediate product in the step (1) in the presence of an oxidizing agent and an organic solvent to obtain a second intermediate product;

[0051] (3) Reductive amination reaction of the second intermediate product and the amino compound in the presence of an organic solvent and a reducing agent in the step (2) to obtain a diol-type ginsenoside having a structure shown in formula I or formula II derivative;

[0052] Wherein, in the step (1), the parent compound has the structure shown in formula IV or V:

[0053]

[0054] In the present invention, the...

Embodiment 1

[0098] Mix 1g (16mmol) of the compound having the structure shown in formula III with 10mL of acetic anhydride and 10mL of pyridine, and perform a nucleophilic substitution reaction at 40°C and 900rpm magnetic stirring for 3h; distill the obtained crude product with 6mL Ethyl acetate was mixed, and the silica gel was used for column chromatography after mixing the sample. The mixture of ethyl acetate and n-hexane was used as the eluent (the volume ratio of ethyl acetate and n-hexane was 1:5), and 1.3 g of white solid was obtained. Compound 1, yield 90%. The structure of the compound 1 is:

[0099]

Embodiment 2

[0101] Mix 1g (11mmol) of the compound 1 prepared in Example 1, 5mL of dichloromethane, and 0.2g (11mmol) of m-chloroperoxybenzoic acid, and carry out the primary oxidation reaction at room temperature for 1h; Add 25mL of water to the material, stir it magnetically at 1100rpm for 1h, a white solid precipitates out, filter to obtain a clear solution, distill off the solvent under reduced pressure, mix the obtained crude product with 8mL of ethyl acetate, mix the sample with silica gel, and use it for column chromatography. Using a mixture of ethyl acetate and n-hexane as the eluent (the volume ratio of ethyl acetate and n-hexane is 1:8), 0.87 g of compound 2 was obtained as a white solid with a yield of 90%. The structure of the compound 2 is:

[0102]

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Abstract

The invention provides a peotopanaxadiol ginsenoside derivative with a structure shown as formula I or a formula II and provides application of the peotopanaxadiol ginsenoside derivative to preparation of drugs for preventing and curing atherosclerosis. The peotopanaxadiol ginsenoside derivative has the advantages that the peotopanaxadiol ginsenoside derivative is low in cytotoxicity and capable of decreasing the percentage of the apoE- / -mouse atherosclerotic plaque area, reducing medium-low density lipoprotein cholesterol level in mouse serum effectively and raising high-density lipoprotein cholesterol level effectively; the peotopanaxadiol ginsenoside derivative is capable of reducing partial TNF-alpha level of apoE- / -mouse arteries, thereby having a good anti-inflammatory effect; the peotopanaxadiol ginsenoside derivative is capable of reducing RAW264.7 cell-derived foam cell forming degree under a dosage of 30 micron remarkably. The invention further provides a preparation method of the peotopanaxadiol ginsenoside derivative. The preparation method is simple and convenient to implement and high in yield.

Description

technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to diol-type ginsenoside derivatives and their preparation methods and applications. Background technique [0002] Atherosclerosis is one of the diseases with high morbidity in today's society. It is the common pathological basis of many serious cardiovascular diseases (such as coronary heart disease, angina pectoris, cerebral vascular embolism, etc.), which seriously threatens human health. Currently, drugs for the treatment of atherosclerosis mainly regulate blood lipids, including statins, fibrates, and niacin. Although the above categories of drugs can achieve a good effect of lowering blood lipids, the incidence of atherosclerosis remains high and increases year by year, which shows that drugs that only have the function of regulating blood lipids cannot meet the needs of prevention and treatment of atherosclerosis . Studies have shown that inflammatory immune fa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J41/00C07J43/00C07H15/18C07H1/00A61P9/10
CPCC07H1/00C07H15/18C07J41/0033C07J43/003C07J41/0055A61P9/10A61K31/575A61K31/58A61K31/70C07J17/005C07J41/005C07J17/00
Inventor 李晓辉贾乙黄琰
Owner ARMY MEDICAL UNIV
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