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1-Deoxynojirimycin-methyl hydroxycinnamate hybrid derivative and preparation method and application thereof

A technology of deoxynojirimycin and derivatives, which is applied in the fields of medicine and food, can solve the problems of hindering disaccharide decomposition and general effect, and achieve the effect of reducing postprandial blood sugar

Active Publication Date: 2019-02-01
JIANGXI AGRICULTURAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

1-Deoxynojirimycin (1-DNJ) is one of the most studied imino sugars. It has a chemical structure similar to glucose and has a greater affinity with α-glucosidase than disaccharides, which can hinder the synthesis of disaccharides. It is a potent competitive α-glucosidase inhibitor, but the substance is absorbed quickly in the body and is metabolized quickly, so the effect of inhibiting the rise of blood sugar after meals in the body is general

Method used

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  • 1-Deoxynojirimycin-methyl hydroxycinnamate hybrid derivative and preparation method and application thereof
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  • 1-Deoxynojirimycin-methyl hydroxycinnamate hybrid derivative and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0039] Example 1: Preparation of 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative DMC-2

[0040] (1) The intermediate preparation of the methyl hydroxycinnamate of the connecting bridge:

[0041]Add 4g (22.44mmol) methyl p-hydroxycinnamate and 8.4g (44.88mmol) 1,2-dibromoethane raw materials into a 250mL round bottom flask, then add 6g (44.88mmol) potassium carbonate and 100mL acetone, Stir and react at 65°C until the end of the reaction; after the end of the reaction, pour the above reaction solution into water, extract with 20 mL of ethyl acetate, repeat the extraction 3 times, and combine the organic phases; dry with anhydrous sodium sulfate, Then desolvation and mixing sample, adopt silica gel column chromatography to separate, eluent is sherwood oil / ethyl acetate=20:1, has made the p-hydroxycinnamic acid methyl ester that has inserted the connecting bridge of 2 carbon atoms Intermediate; 1 H NMR (500MHz, DMSO) δ7.68(d, J=8.7Hz, 2H), 7.63(d, J=16.0Hz, 1H), 7....

Embodiment 2

[0044] Example 2: Preparation of 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative--DMC-6

[0045] (1) The intermediate preparation of the methyl hydroxycinnamate of the connecting bridge:

[0046] Add 4g (22.44mmol) methyl p-hydroxycinnamate and 10.95g (44.88mmol) 1,6-dibromohexane raw materials into a 250mL round bottom flask, then add 6g (44.88mmol) potassium carbonate and 100mL acetone, Stir and react at 65°C until the end of the reaction; after the end of the reaction, pour the above reaction solution into water, extract with 20 mL of ethyl acetate, repeat the extraction 3 times, and combine the organic phases; dry with anhydrous sodium sulfate, Then desolvation and mixing sample, adopt silica gel column chromatography to separate, eluent is sherwood oil / ethyl acetate=20:1, makes the p-hydroxycinnamic acid methyl ester that has inserted the connection bridge of 6 carbon atoms Intermediate; 1 H NMR (500MHz, DMSO) δ7.66(d, J=8.4Hz, 2H), 7.61(d, J=16.0Hz, 1H), 6...

Embodiment 3

[0049] Example 3: Preparation of 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative DMC-5

[0050] (1) The intermediate preparation of the methyl hydroxycinnamate of the connecting bridge:

[0051] Add 4g (22.44mmol) methyl p-hydroxycinnamate and 10.31g (44.88mmol) 1,5-dibromopentane raw materials into a 250mL round bottom flask, then add 6g (44.88mmol) potassium carbonate and 100mL acetone, Stir and react at 65°C until the end of the reaction; after the end of the reaction, pour the above reaction solution into water, extract with 20 mL of ethyl acetate, repeat the extraction 3 times, and combine the organic phases; dry with anhydrous sodium sulfate, Then desolvation and mixing sample, adopt silica gel column chromatography to separate, eluent is sherwood oil / ethyl acetate=20:1, has made the p-hydroxycinnamic acid methyl ester that has inserted the connecting bridge of 5 carbon atoms Intermediate; 1 H NMR (500MHz, DMSO) δ7.66(d, J=8.7Hz, 2H), 7.61(d, J=16.0Hz, 1H)...

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Abstract

The invention relates to the field of medicine and food, in particular to 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative and a preparation method and application thereof. The 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative has a structure shown as formula (I); in-vitro text proves that the 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative is an efficient alpha-glucosidase inhibitor evidently more active in inhibiting alpha-glucosidase than the post-diet glucose controller, acarbose, the most common at present. As the 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative can efficiently inhibit activity of sugar digestive enzymes, such as alpha-glucosidase and effectively lower post-diet glucose, the 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative has a promising application prospect in hypoglycemic drugs and auxiliary hypoglycemic foods.

Description

technical field [0001] The invention relates to the fields of medicine and food, in particular to a 1-deoxynojirimycin-methyl hydroxycinnamate hybrid derivative and a preparation method and application thereof. Background technique [0002] Hyperglycemia is an important cause of diabetic complications, and controlling blood sugar levels is very important for patients with hyperglycemia. Taking carbohydrate-digesting enzyme inhibitors such as α-glucosidase and amylase is one of the first-choice methods to control postprandial blood sugar and treat type 2 diabetes. Therefore, it is of great significance to develop highly active carbohydrate-digesting enzyme inhibitors. The reported inhibitors of carbohydrate digestive enzymes are mainly discovered through natural product screening. Discovering α-glucosidase inhibitors from natural resources, especially natural animal, plant and microbial resources with hypoglycemic activity, is an important task in the past few decades. In re...

Claims

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Application Information

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IPC IPC(8): C07D211/44A61K31/445A61P3/10A23L7/104A23L33/10
CPCA23L7/104A23L33/10A23V2002/00A61P3/10C07D211/44A23V2200/328A23V2250/76
Inventor 尹忠平林萍彭大勇上官新晨蒋艳陈继光曾凡新
Owner JIANGXI AGRICULTURAL UNIVERSITY
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