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Mangiferin hepta-propyl-esterified derivative

A compound, the technology of propionic anhydride, applied in the field of mangiferin heptapropyl esterification derivatives, can solve the problems of poor gastrointestinal permeability of mangiferin, poor permeability of mangiferin, poor absorption effect, etc.

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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  • Mangiferin hepta-propyl-esterified derivative
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  • Mangiferin hepta-propyl-esterified derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0013] Operate in a water bath, add 3ml of 98% H 2 SO 4 , then add 10g of mangiferin after dripping; place the solution at 60°C to keep warm, react for 36 hours, stir from time to time to dissolve all mangiferin; after the reaction is complete, pour the reaction solution directly into water under constant stirring ; The insoluble matter was filtered to obtain the reaction product; the reaction product was mixed with silica gel, put on the top of the silica gel dry column, and was first eluted with chloroform, then eluted with chloroform: methanol=25: 1, collected fractions, evaporated to dryness, Obtain crude crystals; recrystallize the crude crystals with methanol 2-3 times to obtain mangiferin heptapropyl esterified derivatives.

Embodiment 2

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

[0015] Operate in a water bath, add 10ml of 36% HCl dropwise to 250ml of propionic anhydride under constant stirring, and then add 10g of mangiferin after dropping; keep the solution at 70°C for 18 hours of reaction, stirring from time to time 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:methanol=25:1, collected fractions, evaporated to dryness, to obtain crude crystals; the crude crystals were recrystallized 2-3 times with methanol to obtain mangiferin heptapropyl esterified derivatives.

Embodiment 3

[0016] Embodiment 3: anti-inflammatory pharmacological experiment and result

[0017] Mouse auricle swelling test 40 mice were randomly divided into 4 groups. Set up normal control group, aspirin group (0.2g / kg), mangiferin heptapropyl ester derivative group (0.45g / kg, 0.25g / 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 micro-syringe, and the mouse was killed by pulling the cervical spine 15 min later. 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 results are shown in Tab...

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Abstract

The invention discloses a method for chemically synthesizing a mangiferin hepta-propyl-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 mostly found in the fruits, leaves, and bark of Mango (Mangifera indica L.), the rhizome and aerial parts of Anemarrhena asphodeloides Bge., and Belamcanda chinensis (Belamcanda chinensis). (L.) DC.) in flowers, leaves and other plants. [0003] [0004] The solubility of mangiferin is poor (the average solubility in pure water and pH 1.3-7.4 buffer solution is <1 mg·mL -1 ), and the converted human oral effective dose is 630 mg. According to the definition of the Biopharmaceutics classification system (BCS), mangiferin belongs to a poorly soluble drug. In addition, the distribution coefficient (Oil / water partition coefficient, P) of mangiferin in n-butanol-water system is very small (when the...

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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