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Compounds like quercetol and metal complex of their glycosides and uses

The technology of metal complexes and compounds is applied in the application field of preparing medicines for the treatment of diabetes, can solve the problems of low bioavailability, low activity, large toxic and side effects, etc., achieve good α-glucosidase inhibitory activity, improve diabetes Complications, the effect of reducing postprandial hyperglycemia

Inactive Publication Date: 2006-08-16
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, simple metal ions have low fat solubility, low bioavailability, low activity, and require a large dose, so the toxic and side effects are also very large, and have no clinical application value.

Method used

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  • Compounds like quercetol and metal complex of their glycosides and uses
  • Compounds like quercetol and metal complex of their glycosides and uses
  • Compounds like quercetol and metal complex of their glycosides and uses

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] Example 1: Synthesis of quercetin vanadyl complex

[0018] Dissolve 10mmol quercetin in 70mL absolute ethanol solution, add 5mmol VOSO dropwise 4 ·3H 2 The aqueous solution of O was heated to 60° C., refluxed and stirred for 12 hours. After cooling to room temperature, an appropriate amount of water was added and allowed to stand for 30 hours. After suction filtration, the precipitate was washed several times with ethanol and water respectively, and then vacuum dried for 48 hours to obtain a dark blue powdery solid product.

[0019] Product structure:

[0020]

[0021] Product structure analysis data:

[0022] 1 HNMR(300MHz, DMSO-d 6 )δ: 11.60(1H,5-OH); δ10.74(1H,7-OH); δ9.32(1H,4′-OH); δ9.25(1H,3′-OH); δ7.93 (1H, H-2'); δ7.12(1H, H-6'); δ6.71(1H, H-5'); δ6.54(1H, H-8); δ6.31(1H, H-6); δ3.0~3.6(HO). m / z: 753.1 (M+).

[0023] The synthesis methods of other quercetin compounds and their glycoside vanadyl complexes are basically the same as the above methods.

Embodiment 2

[0024] Example 2: Synthesis of quercetin zinc complex

[0025] 5mmol zinc acetate was added to 70mL anhydrous ethanol solution containing 10mmol quercetin and an appropriate amount of sodium acetate, and the reaction was stirred under reflux for 10 hours, and a yellow flocculent precipitate was formed. After cooling to room temperature, add appropriate amount of water, leave it for 24 hours, and filter with suction. After washing the precipitate several times with ethanol and water respectively, it was dried in vacuum for 48 hours to obtain a yellow powdery solid product.

[0026] Product structure:

[0027]

[0028] Product structure analysis data:

[0029] 1 HNMR(300MHz, DMSO-d 6 )δ: 11.63(1H,5-OH); δ10.74(1H,7-OH); δ9.32(1H,4′-OH); δ9.25(1H,3′-OH); δ7.93 (1H, H-2'); δ7.12(1H, H-6'); δ6.71(1H, H-5'); δ6.54(1H, H-8); δ6.31(1H, H-6); δ3.0~3.6(HO). m / z: 690.1 (M+).

[0030] The synthesis methods of other quercetin compounds and their glycoside zinc complexes are basically the sam...

Embodiment 3

[0031] Example 3: Synthesis of copper quercetin complex

[0032] Add 5mmol of copper acetate to 70mL of absolute ethanol solution containing 10mmol of quercetin and an appropriate amount of sodium acetate, reflux and stir the reaction for 10 hours, a green flocculent precipitate is produced. After cooling to room temperature, add an appropriate amount of water and leave it for 48 hours. Suction filtration. After washing the precipitate several times with ethanol and water respectively, it was vacuum dried for 40 hours to obtain a green powdery solid product.

[0033] Product structure:

[0034]

[0035] Product structure analysis data:

[0036] 1 HNMR(300MHz, DMSO-d 6 )δ: 11.63(1H,5-OH); δ10.74(1H,7-OH); δ9.32(1H,4′-OH); δ9.25(1H,3′-OH); δ7.93 (1H, H-2'); δ7.12(1H, H-6'); δ6.71(1H, H-5'); δ6.54(1H, H-8); δ6.31(1H, H-6); δ3.0~3.6(HO). m / z: 716.1 (M+).

[0037] The synthesis methods of other quercetin compounds and their glycoside zinc complexes are basically the same as the above...

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PUM

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Abstract

A quercetin compound, its glucoside metal compounding material and use are disclosed. In structural formula, M, R1 R2 R3 and R4 are determined in specifications. It has excellent inhibiting activity for alpha-glucosidease and can be used to prepare medicine for treating and preventing diabetes mellitus.

Description

Technical field [0001] The invention relates to quercetin compounds and metal complexes of glycosides, and the application of such metal complexes in preparing medicines for treating diabetes. Background technique [0002] Diabetes mellitus is a syndrome of endocrine and metabolic disorders, characterized by continuous increase in blood sugar and urine sugar, and is one of the most common metabolic endocrine diseases in humans. Diabetes is mainly divided into two types: type I diabetes (insulin-dependent) and type II diabetes (non-insulin-dependent). Among them, type II diabetes has a surge trend in recent years. The direction of research on the treatment of type II diabetes is to develop convenient oral drugs. The main drugs currently used clinically include sulfonylureas, biguanides and α-glucosidase inhibitors, but they all have certain toxic and side effects. [0003] Alpha-glucosidase is an important enzyme system in the metabolism of carbohydrates in the human body, and has...

Claims

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Application Information

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IPC IPC(8): C07H17/07C07F9/00C07F3/06C07F1/08C07F11/00C07F3/02C07F13/00A61K31/7048A61K9/08A61K9/20A61K9/48A61K9/10A61P3/10
Inventor 古练权王愉芳黄志纾徐刚黄民李月明陈新滋
Owner SUN YAT SEN UNIV
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