Puerarin derivatives and their medical uses

A technology of puerarin and tetraacetyl puerarin, applied in the field of puerarin derivatives, can solve the problems of low bioavailability, limited use, and limited clinical application range of puerarin

Active Publication Date: 2006-04-26
THE HONG KONG POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Therefore, the low bioavailability limits the use of the above-mentioned puerarin in medical treatment, and because of this, the clinical application range of puerarin is very small, and it is only used for injection therapy

Method used

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  • Puerarin derivatives and their medical uses
  • Puerarin derivatives and their medical uses
  • Puerarin derivatives and their medical uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Synthesis and structure identification of embodiment 1 compound I-III

[0020] 1.1 The synthesis of compound I-III comprises the following steps:

[0021] (1) 50g of puerarin (purity 99%, Shaanxi Huike Plant Technology Co., Ltd., China) was dissolved in 600ml of pyridine, and 100g of anhydrous acetic anhydride was added, stirred at room temperature for 30 minutes, and left at room temperature for 24 hours to obtain the mixture That is reactant A.

[0022] (2) Slowly pour reactant A into 10L of ice water, stir well and filter under reduced pressure to obtain approximately 80 g of reactant B.

[0023] (3) Dissolve reactant B in dichloromethane and add 5% sodium carbonate solution, fully stir at room temperature for 1 hour, separate the organic phase, and evaporate to obtain about 70 g of anhydrous reactant C.

[0024] (4) C is poured into a chromatographic column equipped with 5000 g of silica gel H (10-40 μ, Qingdao Ocean Chemical Factory). The eluent is a mixture o...

example 2

[0060] Example 2: Study on the bioavailability of orally administered puerarin derivatives:

[0061] 2.1 Materials

[0062] 2.1.1 Agents and reagents

[0063] Puerarin was purchased from Beijing United Pharmaceutical Factory (People's Republic of China, PRC, lot number: 030404). The purity was 99% by high performance liquid chromatography (HPLC). Puerarin derivatives 4ac, 5ac, and 6ac can be synthesized by the above method, provided by Hong Kong Polytechnic University, and their analyzed purity is over 98%. Both acetonitrile and methanol were of HPLC grade and double distilled water was used.

[0064] 2.1.2 Instrument and chromatographic conditions

[0065] Agilent1100HPLC, DAD diode, HP1100 chromatography workstation, AgilentXDB-C 18 Column (250mm×4.6mmD, 5μm), the pre-chromatographic column is AgilentXDB-C 18 Column (12.5 mm x 4.6 mm D, 5 μm). Gradient elution is carried out according to the following table 1:

[0066] Table 1 Chromatographic conditions

[0067] ...

Embodiment 3

[0109] Embodiment 3: The effect of puerarin and its derivatives in the treatment of the disease caused by the injection of the posterior pituitary extract Efficacy of acute myocardial ischemia in rats

[0110] 3.1 Materials

[0111] 3.1.1 Test compounds

[0112] Puerarin was purchased from Beijing United Pharmaceutical Factory (China). Derivatives 4ac, 5ac and 6ac of puerarin were provided by Hong Kong Polytechnic University. Puerarin was dissolved in 1:1 PEG400 and sterilized distilled water to prepare 0.8g / kg body weight and 10ml / kg body weight solution for intragastric feeding .

[0113] The puerarin derivative 4ac was dissolved in 1:1 PEG400 and sterile distilled water to prepare a 1.12 g / kg, 10 ml / kg solution for intra-gastro feeding. Dissolve 5ac in 1:1 PEG400 and sterile distilled water to prepare 1.20g / kg, 10ml / kg solution for intragastric feeding. Dissolve 6ac in 1:1 PEG400 and sterile distilled water to prepare 1.28g / kg, 10ml / kg solution for intragastric feed...

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Abstract

The present invention provides acetylated derivatives of puerarin that have higher bioavailability and are particularly suitable for oral administration. The present invention also teaches that medicaments made of acetylated puerarin derivatives can be used to treat myocardial ischemia, regulate blood lipids, enlarge coronary and cerebral arteries and cardiovascular systems, reduce oxygen consumption of cardiomyocytes, improve microcirculation and prevent platelets Cohesion.

Description

technical field [0001] The present invention relates to puerarin derivatives with stronger bioavailability and production methods thereof. Background technique [0002] Puerarin is an active substance extracted from Pueraria lobata. Its effectiveness in regulating blood lipids, expanding coronary and cerebral arteries, reducing oxygen consumption of cardiomyocytes, and improving microcirculation has long been known. It also has the function of preventing platelet aggregation. [0003] The general formula of puerarin is as figure 1 As shown, R1, R2, and R3 are all hydrogen atoms. Its low bioavailability is mainly attributed to the glucosyl group, because the glucosyl group makes puerarin insoluble in oil and thus difficult to be absorbed by the body. [0004] Therefore, low bioavailability greatly limits the use of the above-mentioned puerarin in medical treatment, and because of this, the scope of clinical application of puerarin is very small, and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/34A61K31/352A61K31/7048A61P3/06C07H17/07
CPCC07H17/00A61P3/06A61P9/00A61P9/10
Inventor 杨大坚李月明陈士林陈新滋
Owner THE HONG KONG POLYTECHNIC UNIV
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