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The preparation method of 7-o-ethyl morroniside

A technology of ethyl morronoside and ethanol, applied in the field of medicine, can solve the problems of low content, separation and purification can not well satisfy pharmacological activity research, no systematic research on pharmacological activity, etc., and achieves less impurities and reaction technology. Reasonable design and low cost effect

Active Publication Date: 2018-06-26
JIANGSU PROVINCIAL HOSPITAL OF TCM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

7-O-Ethylmorroniside is an iridoid glycoside component in cornus (content is about 0.05-0.06mg / g), which contains the morroniside skeleton structure, but whether it has morroniside Similar pharmacological activity has not been systematically studied
Since the content of 7-O-ethyl morroniside in cornus decoction pieces is relatively small, the separation and purification from the decoction pieces cannot better meet the needs of pharmacological activity research in vivo and in vitro

Method used

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Examples

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Effect test

Embodiment 1

[0027] The preparation method of 7-O-ethyl morroniside, comprises the following steps:

[0028] (1) Dissolving: Weigh 1 kg of the total iridoid glycosides of Corni officinalis (containing 40% morroniside and 20% loganin), add 10L of absolute ethanol, and stir at room temperature to disperse it evenly;

[0029] (2) adjust the pH value: add an appropriate amount of dilute phosphoric acid to adjust the pH=3;

[0030] (3) Heating reaction: reflux at 80°C for 16 hours; filter to obtain extract, concentrate to obtain extract;

[0031] (4) Purification and crystallization: add ethyl acetate to the extract to dissolve, filter out the insoluble matter, concentrate the filtrate to a small volume, add dichloromethane to the concentrated solution and stir until there is precipitation, leave to crystallize, and then use ethyl acetate to dissolve the crystallization The ester was dissolved, recrystallized by adding dichloromethane, filtered and dried under reduced pressure to obtain 365 g ...

Embodiment 2

[0033] The preparation method of 7-O-ethyl morroniside, comprises the following steps:

[0034] (1) Dissolving: Weigh 1 kg of total iridoid glycosides of Cornus officinalis (containing 40% morroniside and 20% loganin), put it into an extraction tank, add 15L of absolute ethanol, and stir under normal temperature to make it evenly dispersed;

[0035] (2) adjust the pH value: add an appropriate amount of dilute sulfuric acid to adjust the pH=2;

[0036] (3) Heating reaction: reflux at 90°C for 16 hours; filter to obtain extract, concentrate to obtain extract;

[0037] (4) Purification and crystallization: add ethyl acetate to the extract to dissolve, filter to remove insoluble matter, concentrate the filtrate to a small volume, add dichloromethane to the concentrated solution and stir until there is precipitation, leave to crystallize, and then use ethyl acetate to dissolve the crystallization The ester was dissolved, recrystallized by adding dichloromethane, filtered and dried...

Embodiment 3

[0039] The preparation method of 7-O-ethyl morroniside, comprises the following steps:

[0040] (1) Dissolving: Weigh 1 kg of the total iridoid glycosides of Corni officinalis (containing 40% morroniside and 20% loganin), add 20L of absolute ethanol, and stir at room temperature to disperse it evenly;

[0041] (2) adjust the pH value: add an appropriate amount of dilute hydrochloric acid to adjust the pH=1;

[0042] (3) Heating reaction: reflux extraction at 100°C for 16 hours; filter to obtain extract, concentrate to obtain extract;

[0043] (4) Purification and crystallization: add ethyl acetate to the extract to dissolve, filter out the insoluble matter, concentrate the filtrate to a small volume, add dichloromethane to the concentrated solution and stir until there is precipitation, leave to crystallize, and then use ethyl acetate to dissolve the crystallization Dissolve the ester, add dichloromethane for recrystallization, filter and dry under reduced pressure to obtain ...

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Abstract

The invention discloses a preparation method of 7-O-ethyl morroniside. The best preparation process of 7-O-ethyl morroniside was screened out through a large number of experiments, including dissolution method, reaction pH value, heating temperature, heating time and other parameters, and the best purification method was optimized, and the entire reaction process design Reasonable, strong operability, high synthesis rate of 7‑O‑ethyl morroniside, less impurities, high purity, low cost, and industrial production can be realized. The present invention is further screened through in vivo and in vitro anti-inflammatory experiments, and the results show that 7-O-ethyl morroniside has good anti-inflammatory effects both in vivo and in vitro, and has the potential use of being prepared as an anti-inflammatory drug.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of 7-O-ethyl morroniside, which belongs to the technical field of medicine. Background technique [0002] Cornus officinalis is the dried and mature pulp of Cornus officinalis, a plant in the family Cornaceae, and it is one of the 40 most commonly used precious Chinese medicines. Modern studies have shown that iridoid glycosides are important active substances of Cornus officinalis, which have anti-inflammatory, hepatoprotective, and immunosuppressive activities. Current pharmacological studies have initially revealed the activities of morroniside, loganin, and cornus glycosides, while the pharmacological effects of other iridoid glycosides are still unclear. Literature studies have shown that morroniside can improve diabetic complications and reduce cerebral ischemic damage, and has anti-inflammatory, anti-oxidative, and neuroprotective activities. 7-O...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H17/04C07H1/00A61P29/00
CPCC07H1/00C07H17/04
Inventor 刘志辉郑啸王丽灵王琼陈慧姜誉弘
Owner JIANGSU PROVINCIAL HOSPITAL OF TCM
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