Application of E ring benzyloxy substituted silybin in preparing glycosidase inhibitors

A technology of silibinin and inhibitors, which is applied in the pharmaceutical application field of glycosidase inhibitors prepared by replacing silibinin with E ring benzyloxy, and can solve problems such as diabetes that has not been effectively developed and has not been found to inhibit glycosidase , to achieve the effect of clear industrialization prospects, strong inhibition of α-glucosidase, energy saving and emission reduction in large-scale production

Inactive Publication Date: 2012-12-26
DALI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But it is obvious: the above studies have only focused on the antioxidant and cytoprotective effects of silybin flavonoid lignans
[0007] Although the flavonoid lignan compounds represented by silibinin and dehydrosilibinin have the above-mentioned antioxidant effects, there are no reports on their use in inhibiting glycosidase and treating diabetes
Flavonoid lignans are used in the preparation of drugs for the treatment of type II diabetes, especially their new use for inhibiting α-glucosidase has not been effectively developed. The active compound, that is, the structural modification of flavonoid lignans to have the effect of treating type 2 diabetes is a new field

Method used

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  • Application of E ring benzyloxy substituted silybin in preparing glycosidase inhibitors
  • Application of E ring benzyloxy substituted silybin in preparing glycosidase inhibitors
  • Application of E ring benzyloxy substituted silybin in preparing glycosidase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 : Formula (1) (±)-2-[2,3-dihydro-3-(3-benzyloxy-4-hydroxyphenyl)-2-hydroxymethyl-1,4-benzodioxane Cyclo-6]-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one Preparation instruments and reagents:

[0020] The ultraviolet spectrum was measured with a Shimadzu UV-240 ultraviolet spectrophotometer; the hydrogen nuclear magnetic resonance spectrum 1 H-NMR is measured by INOVA type superconducting nuclear magnetic resonance spectrometer (VARIAN INOVA-400MHz) (tetramethylsilyl ether TMS is internal standard); Electrospray mass spectrometry ESI-MS is measured by Bruker Esquire3000+mass spectrometer, column chromatography uses silica gel ( 100-200, 200-300 and 300-400 mesh) and silica gel GF254 (10-40 mesh) for thin-layer chromatography are produced by Qingdao Ocean Chemical Factory; all reagents used are analytically pure; preparative thin-layer chromatography (PTLC) The aluminum foil silica gel plate of Merck Company was used; the dextran gel Sephadex LH-20 used f...

Embodiment 2

[0033] Example 2 : Compound (1) (±)-2-[2,3-dihydro-3-(3-benzyloxy-4-hydroxyphenyl)-2-hydroxymethyl-1,4-benzodioxane Inhibitory activity of cyclo-6]-2,3-dihydro-3,5,7-trihydroxy-4H-1-chromen-4-one on α-glucosidase

[0034] 2.1 Instruments and reagents

[0035] 2.1.1 Experimental Instruments

[0036] Microplate reader: ELISA plate reader (Bio-Tek Instruments, USA)

[0037] 2.1.2 Reagents

[0038] α-glucosidase is α-D-glucosidase (Sigma, 500U / ml); 4-nitrophenol-α-D-glucopyranoside (PNPG, Merck), reduced glutathione (Shanghai Shenggong) , Acarbose is Baitangping (Bayer Healthcare Co., Ltd., Beijing).

[0039] 2.2 Test method

[0040] The inhibitory effect of compounds on α-glucosidase was determined by colorimetric method. Add phosphate buffer (67 mmol / L, pH 6.8, 170 microliters), reduced glutathione (1 mg / ml, 5 microliters), α-D-glucosidase (diluted to 0.2U / ml, 25 μl), compound (1) was dissolved in DMSO, diluted with phosphate buffer, 25 μl per well, so that the final co...

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PUM

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Abstract

The invention relates to application of E ring benzyloxy substituted silybin to preparing glycosidase inhibitors and in particular discloses application of E ring benzyloxy substituted silybin ester-type flavonolignans or pharmaceutical salt thereof to preparing drugs for inhibiting alpha-glycosidase and preventing and treating type II diabetes. The flavonolignans has extremely obvious activity for inhibiting alpha-glycosidase and the intensity of activity of the 40mcg / ml flavonolignans for inhibiting alpha-glycosidase reaches 93%. The measured half-inhibitory concentration of the flavonolignans shows that the intensity of activity of the flavonolignans for inhibiting alpha-glycosidase is 13 times that of the positive control drug acarbose. The pharmacodynamics result shows that the flavonolignans or pharmaceutical salt thereof can be expected to be applied to preparing glycosidase inhibitors, especially the drugs for preventing and treating type II diabetes.

Description

technical field [0001] The present invention relates to the technical field of medicine, in particular, the present invention relates to a kind of silybin ester type flavonoid lignan substituted by E-ring benzyloxy group or its pharmaceutically acceptable salt, which is used to prepare α-glucosidase inhibiting, preventing and treating Type II diabetes, that is, non-insulin-dependent diabetes mellitus, the flavonoid lignan has extremely significant inhibitory activity of α-glucosidase, and its inhibitory activity to α-glucosidase at a concentration of 40 μg / ml The intensity reaches 93%, and it is shown by measuring its half inhibitory concentration: the intensity of the flavonoid lignan inhibiting α-glucosidase is 13 times that of the positive control drug acarbose, so the compound or its pharmaceutically acceptable salt, and The pharmaceutical composition prepared with pharmaceutical excipients or carriers allowed by the preparation can be expected to be used as a glycosidase ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/357A61P3/10
Inventor 高鹏飞柴军领吴少辉徐吉山巫秀美赵昱刘吉开
Owner DALI UNIV
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