Pharmaceutical application of p-bromocinnamoyl silybin to preparing glycosidase inhibitors

The technology of silibinin ester and namoyl group is applied in the field of pharmaceutical use of p-bromocinnamoyl silibinin for preparing glycosidase inhibitor, which can solve the problems such as diabetes that have not been inhibited by glycosidase, and achieve industrialization prospects Clear, low pollution, huge social and economic benefits

Inactive Publication Date: 2011-02-09
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 compo...

Method used

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  • Pharmaceutical application of p-bromocinnamoyl silybin to preparing glycosidase inhibitors
  • Pharmaceutical application of p-bromocinnamoyl silybin to preparing glycosidase inhibitors
  • Pharmaceutical application of p-bromocinnamoyl silybin to preparing glycosidase inhibitors

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] Example 1 : Formula (1) (±)-4-bromocinnamic acid [3-(4-hydroxyl-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxyl- Preparation of 4-oxo-benzopyran-2)-2,3-dihydro-1,4-benzodioxane-2]-methyl ester

[0020] 1.1 Instruments and reagents:

[0021] 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) Aluminum foil silica gel plates from Merck were used; Sephadex LH-20 f...

Embodiment 2

[0025] Example 2 : Compound (1) (±)-4-bromocinnamic acid [3-(4-hydroxy-3-methoxyphenyl)-6-(2,3-dihydro-3,5,7-trihydroxy- Detection of α-glucosidase inhibitory activity of 4-oxo-benzopyran-2)-2,3-dihydro-1,4-benzodioxane-2]-methyl ester

[0026] 2.1 Instruments and reagents

[0027] 2.1.1 Experimental Instruments

[0028] Microplate reader: ELISA plate reader (Bio-Tek Instruments, USA)

[0029] 2.1.2 Reagents

[0030] 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).

[0031] 2.2 Test method

[0032] The inhibitory effect of compounds on α-glucosidase was determined by colorimetric method. Add phosphate buffer (67 mmol / L, pH6.8, 170 microliters), reduced glutathione (1 mg / ml, 5 microliters), α-D-glucosidase (diluted with phosphate buffer into 0.2U / ml, 25 microliters), compound (1) was dissolved in dimethyl sulfoxide...

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Abstract

The invention relates to pharmaceutical application of p-bromocinnamoyl silybin to preparing glycosidase inhibitors and specifically discloses application of 23-p-bromocinnamoyl substituted silybin ester flavonolignans or medicinal 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 flavonolignans for inhibiting alpha-glycosidase reaches 54.4% under the condition of 4mcg/ml concentration. The measured half-inhibitoryconcentration of the flavonolignans shows that the intensity of activity of the flavonolignans for inhibiting alpha-glycosidase is 76.8 times that of the positive control drug acarbose. The pharmacodynamics result shows that the flavonolignans or medicinal 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 silybin ester type flavonoid lignan substituted with bromocinnamoyl group at the 23rd position or a pharmaceutically acceptable salt thereof for preparing α-glucosidase-inhibiting, Prevention and treatment of type II diabetes, that is, non-insulin-dependent diabetes mellitus, the flavonoid lignan has an extremely significant activity of inhibiting α-glucosidase, and it inhibits α-glucosidase at a concentration of 4 micrograms / ml The activity intensity has reached 54.4%, and it shows by measuring its half maximal inhibitory concentration: the intensity of the flavonoid lignan to inhibit α-glucosidase is 76.8 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...

Claims

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Application Information

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IPC IPC(8): A61K31/357A61P3/10
Inventor 张海林吴昊汤珺李建昌巫秀美赵昱马海滨
Owner DALI UNIV
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