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Method for preparing ursolic acid derivative 3-o-keto-12-alkenyl-28-ursolic acid

A technology of ursolic acid and ethyl acetate, applied in the field of natural medicine, can solve the problems of difficult separation of product and catalyst, low yield, and total yield of only 80%, and achieves rapid separation, high product purity, and simple operation. Effect

Inactive Publication Date: 2011-01-19
ARMY MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yet, in the preparation process of 3-O-keto-12-ene-28-ursolic acid, need to adopt onium chlorochromate (PCC) as oxidizing agent, after onium chlorochromate reacts, sticky matter is formed, making It is very difficult to separate the product from the catalyst, resulting in a low yield, the total yield is only about 80% [Gnoatto, S.C.B., Klimpt, A.D., Nascimento, S.D., Galera, P., Boumediene, K., Gosmann, G., Sonnet, P., Moslemi, S. European Journal of Medicinal Chemistry, 2008, 43: 1865-1877.]

Method used

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  • Method for preparing ursolic acid derivative 3-o-keto-12-alkenyl-28-ursolic acid
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  • Method for preparing ursolic acid derivative 3-o-keto-12-alkenyl-28-ursolic acid

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Effect test

Embodiment 1

[0020] ① Dissolve 1.11g of ursolic acid in 10ml of dry dichloromethane, cool in an ice bath, then add 0.6g of pyridinium chlorochromate, stir and react for 4 hours, remove the ice bath, and react at room temperature for 8 hours.

[0021] ② Concentrate and dry the above-mentioned reaction solution under reduced pressure, then extract the product with butanol 3 times, 10ml each time, filter, combine the organic phases, and concentrate under reduced pressure at 30°C to obtain 3-O-keto-12-ene-28 - Crude ursolic acid 1.12g.

[0022] ③Separate the crude 3-O-keto-12-ene-28-ursolic acid through a column with 10 g of 300-400 mesh silica gel, apply a dry method to the column, and use ethyl acetate to petroleum ether = 5:1 as the eluent , 1.00 g of pure product was obtained, the yield was 90.0%, and the purity was 99.0% (HPLC test, area normalization method).

[0023] The physical and chemical properties of the isolated 3-O-keto-12-ene-28-ursolic acid are as follows:

[0024] Melting p...

Embodiment 2

[0031] ① Dissolve 22.0g of ursolic acid in 180.0ml of dry dichloromethane, cool in an ice bath, then add 12.5g of pyridinium chlorochromate, stir and react for 4 hours, remove the ice bath, and react overnight at room temperature.

[0032] ②Concentrate the reaction liquid after the above reaction to dryness under reduced pressure, then extract the product with ether 5 times, 30ml each time, filter, combine the organic phases, and concentrate under reduced pressure at 55°C to obtain 3-O-keto-12-ene-28- Crude ursolic acid 21.8g.

[0033] ③Separate the crude 3-O-keto-12-ene-28-ursolic acid through a column with 100 g of 300-400 mesh silica gel, put it on the column by dry method, and use ethyl acetate to petroleum ether = 3:1 as the eluent , 20.9 g of pure product was obtained, the yield was 95.0%, and the purity was 99.0% (HPLC test, area normalization method).

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Abstract

The invention relates to the field of natural medicaments, in particular to a method for preparing 3-o-keto-12-alkenyl-28-ursolic acid. The method is characterized by performing after-treatment on reaction solution to improve the reaction solution on the basis of the conventional reaction method, namely reacting ursolic acid with pyridinium chlorochromate. The after-treatment method of the invention comprises the following steps of: concentrating the reaction solution under reduced pressure; extracting the residual solid by using ethyl ether or butanol; concentrating an organic phase under reduced pressure to obtain a crude product; and allowing the crude product to pass through a silicagel column for elution to obtain the 3-o-keto-12-alkenyl-28-ursolic acid. The preparation method of the invention has the advantages of simple separation method, easy operation and high product yield.

Description

technical field [0001] The present invention relates to the field of natural medicines, in particular to the chemical modification method of natural compound ursolic acid, more specifically, to the synthesis and separation method of ursolic acid derivative 3-O-keto-12-ene-28-ursolic acid, That is, the method of preparing 3-O-keto-12-ene-28-ursolic acid by means of synthesis and separation. Background technique [0002] Ursolic acid (UA), also known as ursolic acid, is a pentacyclic triterpenoid. Ursolic acid is widely distributed in medicinal plants, and has various biological activities such as sedative, anti-inflammatory, antibacterial, anti-diabetic, anti-ulcer, and hypoglycemic. Modern pharmacological studies have found that ursolic acid has obvious anti-tumor effects, including inhibiting tumor cell growth, inducing tumor cell differentiation, anti-tumor tissue angiogenesis and inducing tumor cell apoptosis. These results show that ursolic acid is a promising antitumo...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00
Inventor 高宁刘毅敏张定林刘鄂湖
Owner ARMY MEDICAL UNIV
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