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Berberine glycyrrhizic acid enantiomer salt and preparation method and usage thereof

A technology of glycyrrhizic acid and berberine, which is applied in the preparation of sugar derivatives, chemical instruments and methods, and pharmaceutical formulations, and can solve the problems of insufficient clinical efficacy and therapeutic range of berberine

Inactive Publication Date: 2010-06-23
HANGHZOU HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to solve the deficiency of existing single compound berberine in clinical curative effect and therapeutic range, and to provide a kind of berberine glycyrrhizic acid enantiomer salt whose curative effect is better than that of single compound in the treatment of diabetes, tumor and chronic inflammatory disease

Method used

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  • Berberine glycyrrhizic acid enantiomer salt and preparation method and usage thereof
  • Berberine glycyrrhizic acid enantiomer salt and preparation method and usage thereof
  • Berberine glycyrrhizic acid enantiomer salt and preparation method and usage thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] What this embodiment provides is the preparation method of berberine 18β-glycyrrhizinate:

[0026] Take about 60g of berberine and dissolve it in hot water; add 100g of anion exchange resin (Amberite IR-400) after cooling to room temperature, stir for 1 hour, filter, remove the resin, and put the filtrate into a solution containing 74g of 18β-monoammonium glycyrrhizinate , adjust the pH to about 4.0, stir for 30 minutes, let stand, refrigerate for 24 hours, filter, wash the precipitate twice with a small amount of ice water, drain, dry in vacuum at 60°C, add ethanol to dissolve, and filter. The alcohol solution was vacuum-dried below 60°C to obtain 87g of brown-yellow powder. The yield is 65%.

[0027] mp: 215-218°C

[0028] [C] D20+47.4° (c=0.707, methanol)

[0029]

Embodiment 2

[0031] What this embodiment provides is the preparation method of berberine 18a-glycyrrhizinate:

[0032] Take about 60g of berberine, dissolve it in hot water; take another 74g of 18a-monoammonium glycyrrhizinate, dissolve it in water, adjust the pH to about 4, add it into the above solution under stirring at room temperature, stir for 30min, let stand, and refrigerate for 24 hours, filtered, the precipitate was washed twice with a small amount of ice water, sucked dry, dried in vacuum at 60°C, dissolved in ethanol, and filtered. The alcohol solution was vacuum-dried below 60°C to obtain 94g of brown yellow powder. The yield is 70%.

[0033] mp: 248-254°C

[0034][C] D20+18.3° (c=0.707, methanol)

[0035]

Embodiment 3

[0037] This example describes the effect of compounds provided by the present invention on the blood sugar of alloxan diabetic mice:

[0038] Alloxan was used to create a hyperglycemia model in mice, and the mice with blood glucose > 11mmol / l were randomly divided into groups, model control group, 18β-glycyrrhizinate berberine salt, 18a-glycyrrhizinate berberine salt, and positive control group were given Normal saline, 18β-glycyrrhizinate berberine salt, 18a-glycyrrhizinate berberine salt, berberine, once a day, for 14 consecutive days, fasting for 12 hours after the last administration, without water, test fasting blood sugar, observe medication Changes in blood sugar before and after.

[0039] Table 1 Blood glucose before and after alloxan administration in mice

[0040]

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Abstract

The invention discloses a novel organic salt-a berberine glycyrrhizic acid enantiomer salt which can be used for medicine, and a preparation method and usage thereof. The chemical name of the berberine glycyrrhizic acid enantiomer salt is 5,6-dihydro-9,10-dimethoxy-benzo (g)-1,3-benzo-dioxolane[5,6-a]quinolizidine.18a(beta),20beta-carboxy-11-oxo-30-norolean-12-alkene-3beta-yl-2-O-beta-D-glucopyranuronosyl-a-D-glucopyranosiduronic acid. The preparation method comprises the steps that berberine hydrochloride is dissolved with water according to the pharmaceutical co-crystal principle, anion exchange resin is added, then the mixture is stirred for one hour and filtered, the filtrate is put into a water solution of a glycyrrhizic acid enantiomer and stirred for 30 minutes for centrifugation, the precipitate is dissolved in ethanol, and decompression is carried out to remove the solvent to get the berberine glycyrrhizic acid enantiomer salt. The organic salt with double mother nucleuses has practical significance for human in resisting diabetes, hyperlipidemia, tumor and chronic inflammatory diseases of rheumatoid arthritis, hepatitis, Alzheimer and the like and developing the medical industry.

Description

technical field [0001] The present invention relates to a new compound that can be used in the treatment of diabetes and tumors, specifically a compound salt formed by combining berberine and glycyrrhizic acid, which is 18a-glycyrrhizic acid or 18β-glycyrrhizic acid, which are different enantiomers of berberine and glycyrrhizic acid combined salt. Background technique [0002] Berberine is an isoquinoline alkaloid extracted from Coptis chinensis of the family Ranunculaceae, and is the main component of Chinese medicine Coptis chinensis. In the past, it was often believed that it was not easy to absorb after oral administration, and because it is effective against intestinal infections caused by Shigella, Escherichia coli, and Staphylococcus aureus, conjunctivitis, suppurative otitis media, etc., it is mainly used clinically for the treatment of intestinal infections. With the deepening of research, in recent years, it has been found that it has anti-arrhythmia, vasodilation...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07H15/256C07D455/03C07H1/00A61K31/704A61K31/4375A61P3/10A61P3/06A61P35/00A61P29/00A61P19/02A61P1/16A61P25/28
Inventor 王佩吴锡铭
Owner HANGHZOU HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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