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Use of pentacyclic triterpene compound as glycogen phosphorylase inhibitor

A technology of pentacyclic triterpenoids and compounds, applied in the field of medicine, can solve problems such as the limitation of oxidative energy supply

Inactive Publication Date: 2010-05-12
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, under the condition of cardiomyocyte hypoxia caused by myocardial ischemia, the oxidation supply of fatty acids is limited, and the energy supply of cardiomyocytes thus turns to anaerobic glycolysis (glycolysis)

Method used

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  • Use of pentacyclic triterpene compound as glycogen phosphorylase inhibitor
  • Use of pentacyclic triterpene compound as glycogen phosphorylase inhibitor
  • Use of pentacyclic triterpene compound as glycogen phosphorylase inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0153] Preparation of 3-isomeric oleanolic acid

[0154] Dissolve 0.54 g of 3-carbonyloleanolic acid-28-benzyl ester (9a) in 14 mL of anhydrous isopropanol, add aluminum isopropoxide (24.7%, 2.5 g, commercial product) and a catalytic amount of AlCl 3 , the oil bath was refluxed at about 95°C. After six days, the raw materials had not completely disappeared, and the reflux was stopped. After cooling, 100 mL of 1N hydrochloric acid was slowly added dropwise to the reaction liquid, extracted with 40 mL of ethyl acetate, washed with saturated sodium bicarbonate solution, and finally Wash with saturated brine to obtain an ethyl acetate layer, anhydrous Na 2 SO 4 Drying, evaporation to dryness, and flash column chromatography (petroleum ether: ethyl acetate = 20:1) gave 0.18 g (33.2%) of 3α-hydroxyoleanolic acid-28-benzyl ester.

[0155] Add 8 mL of tetrahydrofuran to 3α-hydroxyoleanolic acid-28-benzyl ester (0.12 g), add 10% Pd / C (0.02 g), and hydrogenate at room temperature and ...

Embodiment 2

[0157] Preparation of 3-isomeric ursolic acid

[0158] With 3-carbonyl ursolic acid-28-benzyl ester (9b) as raw material, 3α-hydroxy ursolic acid was obtained with reference to the method of Example 1.

Embodiment 3

[0160] Preparation of oleanolic acid-28-methyl ester

[0161] Oleanolic acid (5.0g) was dissolved in 50mL of anhydrous DMF, adding K 2 CO 3 (3.0 g) and MeI (0.82 mL), stirred at room temperature for 2.5 hours. After dilution with water, it was extracted with ethyl acetate, and the combined ethyl acetate layer was washed successively with 1 mol / L aqueous hydrochloric acid solution and saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. After distilling off the solvent, 5.36 g of light yellow crude product of methyl oleanolic acid was obtained. Get 0.25g of crude product through silica gel column chromatography (eluent, petroleum ether: ethyl acetate=6:1) to obtain pure product methyl oleanate 0.23g.

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Abstract

An application of the pentacyclo-triterpenoid used as the glycogen phosphorylase for preparing the medicines to treat diabetes, ischemic cardiovascular and cerebrovascular diseases, and tumor is disclosed.

Description

technical field [0001] The present invention relates to the field of medicines, in particular to the use of a series of pentacyclic triterpenoids as glycogen phosphorylase inhibitors, especially in the preparation of antidiabetic drugs, anti-ischemic cardiovascular and cerebrovascular disease drugs, and antitumor drugs. Applications. Background technique [0002] Pentacyclic triterpenoids are widely distributed in the plant kingdom and are the main active ingredients of many Chinese herbal medicines (Sun Hongbin, "Progress in Medicinal Chemistry", 2005, Vol. 4: 253-279). Pentacyclic triterpenoids can be divided into oleane type, arbutane type and lupine type according to the different alkane structure. [0003] The preparation method of the pentacyclic triterpene compound includes a phytochemical extraction method, a semi-synthetic preparation method and the like. International patent applications WO 02 / 12159 and WO 98 / 04331 report methods for extracting Maslinic Acid from...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/56A61K31/58A61P3/10A61P9/10A61P9/04A61P25/00
Inventor 孙宏斌张陆勇李运曼温小安陈军柳军程克光方伟蓉胡苗苗关腾孙世学刘竞天倪沛洲华维一王善治
Owner CHINA PHARM UNIV
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