Mangiferin penta-esterified derivative

A technology of glycoside pentaethyl ester and derivatives, applied in the field of mangiferin pentaethyl esterification derivatives, can solve the problems of poor permeability of mangiferin, poor gastrointestinal permeability of mangiferin, and poor absorption effect.

Inactive Publication Date: 2012-05-02
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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  • Mangiferin penta-esterified derivative
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  • Mangiferin penta-esterified derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1: Preparation of mangiferin pentaethyl esterified derivatives

[0014] Operate in a water bath, add 1.5ml of 98% H to 250ml of acetic anhydride dropwise under constant stirring 2 SO 4 , then add 10g of mangiferin after dripping; place the solution at 40°C to keep warm, react for 24 hours, stir from time to time to dissolve all the mangiferin; after the reaction is complete, pour the reaction solution directly into water under constant stirring ; The insoluble matter was collected by filtration to obtain the reaction product; the reaction product was mixed with silica gel as a sample, put on the top of the silica gel dry column, and was first eluted with chloroform, followed by elution with chloroform: ethyl acetate: acetone=20: 1: 1, and then Elute with chloroform: ethyl acetate: acetone = 7:2:1, collect fractions, evaporate to dryness to obtain crude crystals; recrystallize the crude crystals with methanol 2-3 times to obtain mangiferin pentaethyl esterified ...

Embodiment 2

[0015] Example 2: Preparation of mangiferin pentaethyl esterified derivatives

[0016] Operate in a water bath, add 4ml of 36% HCl dropwise to 250ml of acetic anhydride under constant stirring, and then add 10g of mangiferin after dropping; keep the solution at 50°C for 12 hours, stirring occasionally Dissolve the mangiferin completely; after the reaction is completed, pour the reaction solution directly into water under constant stirring; filter the insoluble matter to obtain the reaction product; mix the reaction product with silica gel, put it on the top of the silica gel dry column, and first use chloroform Elution, followed by elution with chloroform: ethyl acetate: acetone = 20: 1: 1, then elution with chloroform: ethyl acetate: acetone = 7: 2: 1, collected fractions, evaporated to dryness, to obtain crude crystals; The crude crystals are recrystallized 2-3 times with methanol to obtain mangiferin pentaethyl esterified derivatives.

Embodiment 3

[0017] Embodiment 3: anti-inflammatory pharmacological experiment and result

[0018] Mouse auricle swelling test 40 mice were randomly divided into 4 groups. Set up normal control group, aspirin group (0.045g / kg), large and small doses of mangiferin pentaethyl ester derivatives group (0.4g / kg, 0.2g / kg), intragastric administration once a day, normal control group The group was given an equal volume of distilled water for 7 consecutive days. 0.5 h after the last administration, 20 μl of xylene was dripped on the right ear of the mouse with a micropipette, and the mouse was killed by pulling the cervical spine after 15 min. Immediately use a hole punch with a caliber of 6 mm to punch holes along the same part of the left and right auricles of the mice, and then weigh them with an electronic balance of 1 / 10,000, and take the difference in weight (mg) between the two ears as the index of swelling degree , swelling degree=(right ear weight-left ear weight) / right ear weight, the ...

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Abstract

The invention discloses a method for chemically synthesizing a mangiferin penta-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 novel organic compound by using mangiferin as a starting material, and the pharmacological effects of the compound on anti-inflammatory and hypoglycemic aspects. technical background [0002] Mangiferin is a glucose C-glucoside with Xanthone structure (molecular formula C 19 h 18 o 11 , molecular weight 422.34), exist in the fruits, leaves and bark of Mango (Mangifera indica L), the rhizome and aerial parts of Anemarrhena asphodeloides Bge., Belamcanda chinensis (Belamcanda chinensis (L .) DC.) flowers, leaves and other plants. [0003] [0004] The mangiferin molecule has a large planar structure, and its solubility is poor (the average solubility in pure water and pH 1.3-7.4 buffer solution is less than 1 mg·mL -1 ), and the converted human oral effective dose is 630mg, and the liquid volume of the gastrointestinal tract required to dissolve a single dose of mangiferin is >250mL. According t...

Claims

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Application Information

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Patent Type & Authority Applications(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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