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Application of L-ascorbyl glycoside compounds to preparation of alpha-glucosidase inhibitors

A technology of glucosidase and acid-based glycosides, which is applied in the field of L-ascorbic acid-based glycosides

Active Publication Date: 2016-01-27
HUAZHONG AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that 2-O-β-D-glucosyl-L-ascorbic acid exhibits better antioxidant activity than vitamin C, (Biosci.Biotechnol.Biochem.2008,72,1558; Journal of Practical Medicine 2011,27,11 ), but there is no research report that such substances have glycosidase inhibitory activity

Method used

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  • Application of L-ascorbyl glycoside compounds to preparation of alpha-glucosidase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Preparation of 2-O-β-D-glucosyl-L-ascorbic acid

[0010] 3-O-benzyl-5,6-O-isopropylidene ascorbic acid (3.06g, 10mmol) and tetraacetylbromoglucose (4.94g, 12mmol) were added to 60mL of dichloromethane and water mixed solvent, Then add K 2 CO 3 (1.66g, 12mmol) and TBABr (12mmol), stirred at room temperature for 5 hours. Separate the liquid, extract the aqueous phase once with dichloromethane, combine the organic phases, wash twice with citric acid solution, then wash once with saturated brine, dry over anhydrous magnesium sulfate, filter, spin the filtrate, and separate by column chromatography 2-O-β-D-tetraacetylglucosyl-3-O-benzyl-L-ascorbic acid (5.09 g, 80%) was obtained.

[0011] 2-O-β-D-tetraacetylglucosyl-3-O-benzyl-L-ascorbic acid (2g, 3.14mmol) was dissolved in 50mL aqueous acetic acid, and reacted at 80°C for 1 hour. After cooling, 50 mL of ethyl acetate was added to the reaction system, washed with water and saturated sodium bicarbonate solution in turn, t...

Embodiment 2

[0014] Preparation of 3-O-β-D-glucosyl-L-ascorbic acid

[0015] 5,6-O-Isopropylidene ascorbic acid (2.00 g, 9.26 mmol) was added to 60 mL of DMF, followed by K 2 CO 3 (1.92g, 14mmol) and tetraacetylbromoglucose (5.71g, 14mmol), stirred at room temperature for 10 hours. Stop the reaction, extract the reaction system with ethyl acetate, wash the organic phase successively with citric acid solution and saturated brine, then dry with anhydrous magnesium sulfate, filter, spin the filtrate to dry, and separate by column chromatography to obtain 3-O-β-D - Tetraacetylglucosyl-L-5,6-O-isopropylidene ascorbic acid (3.31 g, 65%).

[0016] Add 65 mL of acetic acid solution to 3-O-β-D-tetraacetylglucosyl-L-5,6-O-isopropylidene ascorbic acid (1.05 g), and react at 80° C. for 2.5 h. The reaction was stopped, and 50 mL of ethyl acetate was added to the reaction system to extract the product, and the liquid was separated, and the organic phase was followed by water, saturated NaHCO 3 Wash ...

Embodiment 3

[0019] Preparation of 2-O-β-D-galactosyl-L-ascorbic acid

[0020] Add 3-O-benzyl-5,6-O-isopropylidene ascorbic acid (2.45 g, 8 mmol) and tetraacetylbromogalactose (3.95 g, 9.6 mmol) to 50 mL of 60 mL dichloromethane and water mixed solvent , under uniform stirring at room temperature, add K 2 CO 3 (1.33g, 9.6mmol) and TBABr (12mmol), continue stirring for 5 hours. Separate the liquid, extract the aqueous phase once with dichloromethane, combine the organic phases, wash twice with citric acid solution, then wash once with saturated brine, dry with anhydrous magnesium sulfate, filter, spin the filtrate, and perform column chromatography 2-O-β-D-tetraacetylglucosyl-3-O-benzyl-L-ascorbic acid (3.87 g, 76%) was isolated.

[0021] 2-O-β-D-tetraacetylglucosyl-3-O-benzyl-L-ascorbic acid (1.91g, 3mmol) was dissolved in 50mL aqueous acetic acid, and reacted at 80°C for 1 hour. After cooling, 50 mL of ethyl acetate was added to the reaction system, washed with water and saturated sod...

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Abstract

The invention relates to application of L-ascorbyl glycoside compounds, such as 2-O-beta-D-glucosyl-L-ascorbic acid, 3-O-beta-D-glucosyl-L-ascorbic acid and 2-O-beta-D-galactosyl-L-ascorbic acid, to preparation of alpha-glucosidase inhibitors. The L-ascorbyl glycoside compounds are remarkable in alpha-glucosidase inhibition activity and have the inhibition effect approximate to that of voglibose, thereby being developed and applied as the alpha-glucosidase inhibitors.

Description

technical field [0001] The present invention relates to a new application of L-ascorbyl glycoside compounds, especially a new application in the preparation of α-glucosidase inhibitors. Background technique [0002] Diabetes is currently one of the most serious chronic diseases that endanger human health and even life. According to statistics from the International Diabetes Federation, 285 million people worldwide suffered from diabetes in 2010, and it is estimated that the number of patients may reach 438 million by 2030 (Cytotechnology 2015, 67,653). Diabetes is divided into type I diabetes (insulin-resistant type) and type II diabetes (non-insulin-resistant type), and more than 90% of patients belong to type II diabetes. At present, the main treatment method is to control blood sugar by inhibiting glycoside hydrolase. Glycosidase inhibitors can delay the digestion and absorption of sugar, control the sharp rise in blood sugar after meals, and achieve the purpose of balan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/7048A61P3/10C07H17/04C07H1/06
Inventor 马济美江洪谢凌云贾蕊祯董洁曾贞李子龙孙林皓
Owner HUAZHONG AGRI UNIV
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