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Preparation method and pharmacological effect of mangiferin hexa-butyl-esterified derivative

A technology of pharmacological effects and compounds, which is applied in the field of preparation of mangiferin hexabutyl ester derivatives and its pharmacological effects, and can solve problems such as poor absorption effect, poor gastrointestinal permeability of mangiferin, and poor permeability of mangiferin

Inactive Publication Date: 2014-07-02
GUANGXI UNIV OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, the distribution coefficient (Oil / water partition coefficient, P) of mangiferin in n-butanol-water system is very small (when the pH is 1-4, the P value is about 2.3, when the pH value is greater than 6.86, the P value is only 0.01) , usually the P value has a good correlation with the gastrointestinal permeability. When the P value is 100-1000, the passive absorption is better. It is speculated that the gastrointestinal permeability of mangiferin is poor.
Furthermore, mangiferin has poor intestinal absorption in mice, confirming the poor permeability of mangiferin

Method used

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  • Preparation method and pharmacological effect of mangiferin hexa-butyl-esterified derivative
  • Preparation method and pharmacological effect of mangiferin hexa-butyl-esterified derivative
  • Preparation method and pharmacological effect of mangiferin hexa-butyl-esterified derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0012] Example 1: Preparation of mangiferin hexabutyl esterified derivatives

[0013] Operate in a water bath, add 1.5ml 98%H dropwise to 250ml butyric anhydride under constant stirring 2 SO 4 , and then add 10g of mangiferin after dripping; put this solution in a 40°C environment to keep warm, and react for 24 hours, stirring from time to time to dissolve all mangiferin; after the reaction is completed, pour the reaction solution directly into water under constant stirring. The insolubles were collected by filtration to obtain the reaction product; the reaction product was mixed with silica gel, placed on top of a silica gel dry column, first eluted with chloroform, then eluted with chloroform:ethyl acetate:acetone=20:1:1, then Elute with chloroform:ethyl acetate:acetone=7:2:1, collect fractions and evaporate to dryness to obtain crude crystals; the crude crystals are recrystallized with methanol for 2-3 times to obtain mangiferin hexabutyl esterified derivatives.

Embodiment 2

[0014] Example 2: Preparation of mangiferin hexabutyl esterified derivatives

[0015] Operate in a water bath, under constant stirring, add 4ml of 36% HCl dropwise to 250ml of butyric anhydride, and then add 10g of mangiferin; this solution is kept at 50°C for 12 hours of reaction, stirring from time to time. All mangiferin was dissolved; after the reaction was completed, the reaction solution was directly poured into water under the condition of constant stirring; the insolubles were collected by filtration to obtain the reaction product; the reaction product was mixed with silica gel, placed on the top of a silica gel dry column, and chloroform was used first. Elution, followed by chloroform:ethyl acetate:acetone=20:1:1, then chloroform:ethyl acetate:acetone=7:2:1, the fractions were collected and evaporated to dryness to obtain crude crystals; The crude crystals are recrystallized with methanol for 2-3 times to obtain the hexabutyl esterified derivatives of mangiferin.

Embodiment 3

[0016] Example 3: Anti-inflammatory pharmacological experiments and results

[0017] For the mouse ear swelling test, 40 mice were randomly divided into 4 groups. The normal control group, the aspirin group (0.2g / kg), the large and small dose groups of mangiferin hexabutyl ester derivatives (0.4g / kg, 0.2g / kg) were administered by intragastric administration once a day, the normal control group The group was given an equal volume of distilled water for 7 consecutive days. 0.5h after the last administration, 20 μl of xylene was dripped onto the right ear of the mice with a micro-syringe, and the mice were killed by pulling the cervical vertebrae after 15 minutes. Immediately use a hole punch with a diameter of 6 mm to punch holes along the same part of the left and right auricles of the mice, and then use a 1 / 10,000 electronic balance to weigh respectively, and the difference between the weights of the two ear pieces (mg) is used as an indicator of the degree of swelling. , sw...

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Abstract

The invention discloses a method for chemically synthesizing a mangiferin hexa-butyl-esterified derivative and a pharmacological effect of resisting inflammation and reducing blood sugar of the derivative. The chemical structural formula of the derivative is shown in the specifications. The derivative has a remarkable effect of inhibiting mouse auricle tumefaction caused by dimethylbenzene; and the derivative has a remarkable effect of treating diabetic mice induced by alloxan.

Description

technical field [0001] The invention relates to a method for preparing a new organic compound by using mangiferin as a starting material, and the pharmacological effects of the compound in anti-inflammatory and hypoglycemic aspects. technical background [0002] Many Chinese medicinal materials such as the fruit, leaves and bark of Mangifera indica L., the rhizome and aerial part of Liliaceae Anemarrhena asphodeloides Bge., Belamcanda chinensis (L.) DC.) flowers and leaves contain mangiferin (Mangiferin). Mangiferin is a glucose C-glycoside with a Xanthone structure (molecular formula C 19 H 18 O 11 , molecular weight 422.34). [0003] [0004] Mangiferin has a large planar structure and poor solubility (average solubility in pure water and buffer solution with pH 1.3 to 7.4 <1 mg·mL -1 ), and the converted human oral effective dose is 630 mg, and the liquid volume in the gastrointestinal tract required to dissolve a single dose of mangiferin is >250 mL. Accord...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D407/04A61K31/352A61P29/00A61P3/10
Inventor 李学坚杜正彩邓家刚梁建钦刘布鸣黄艳卢文杰
Owner GUANGXI UNIV OF CHINESE MEDICINE
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