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Semi-synthesis method of isoquercetin

A semi-synthetic technology of isoquercetin, applied in the field of biosynthesis, can solve the problems of high equipment performance requirements, difficult purification, low yield and content of isoquercetin, and achieve stable activity, safe and simple operation

Pending Publication Date: 2020-12-22
SHAANXI JIAHE PHYTOCHEM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The purpose of the present invention is to solve the problems of high equipment performance requirements, low yield and content of isoquercetin, and difficult purification when preparing isoquercetin under pressure, and provide a kind of isoquercetin semi-synthetic method

Method used

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  • Semi-synthesis method of isoquercetin

Examples

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Embodiment 1

[0039] A semi-synthetic method for isoquercetin, comprising the following steps:

[0040] 1) Put 12.5g of rutin (95% liquid phase content) in a 500ml three-necked bottle, add 200ml of water, 100ml of ethyl acetate, and 7g of liquid rhamnase; The reaction was stopped by central control for 8 hours to obtain a reaction solution;

[0041] 2) The reaction solution in step 1) was allowed to stand for 4 hours, and the upper ethyl acetate phase and the lower aqueous phase were collected respectively; wherein, the lower aqueous phase was used to prepare rhamnose;

[0042] 3) 3 g of activated carbon is used to decolorize the ethyl acetate phase described in step 2) after reflux for 1 h, and then remove the activated carbon;

[0043] 4) Concentrate the decolorized ethyl acetate phase in step 3) to a small volume, place it to cool and crystallize, and suction filter to obtain 9.3 g of isoquercetin with a purity of 98%. For its liquid chromatogram, see figure 1 .

Embodiment 2

[0045] A semi-synthetic method for isoquercetin, comprising the following steps:

[0046] 1) Put 50g of rutin (95% in liquid phase) in a 2000ml three-necked bottle, add 1000ml of water, 400ml of ethyl acetate, and 35g of liquid rhamnase; Control 8h to stop reaction, obtain reaction solution;

[0047] 2) The reaction solution in step 1) was allowed to stand for 4 hours, and the upper ethyl acetate phase and the lower aqueous phase were collected respectively; wherein, the lower aqueous phase was used to prepare rhamnose;

[0048] 3) 12g of activated carbon is used to decolorize the ethyl acetate phase described in step 2) after reflux for 1h, and then the activated carbon is removed;

[0049] 4) Concentrate the decolorized ethyl acetate phase in step 3) to a small volume, place it to cool and crystallize, and suction filter to obtain 37.8 g of isoquercetin with a purity of 98%. For its liquid chromatogram, see figure 2 .

Embodiment 3

[0051] A semi-synthetic method for isoquercetin, comprising the following steps:

[0052] 1) Put 50kg of rutin (95% in liquid phase) in a 2000L reaction kettle, add 800L of purified water, 400L of ethyl acetate, and 25kg of liquid rhamnase; The reaction was stopped by central control for 12 hours to obtain a reaction solution;

[0053] 2) The reaction solution in step 1) was allowed to stand for 4 hours, and the upper ethyl acetate phase and the lower aqueous phase were collected respectively; wherein, the lower aqueous phase was used to prepare rhamnose;

[0054] 3) 13kg of activated carbon is used to decolorize the ethyl acetate phase described in step 2) after reflux for 1h, and remove the activated carbon;

[0055] 4) Concentrate the decolorized ethyl acetate phase in step 3) to a small volume, place it for cooling and crystallization, and suction filter to obtain 38 kg of isoquercetin with a purity of 98%. For its liquid chromatogram, see image 3 .

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Abstract

The invention provides a semi-synthesis method of isoquercetin, and solves the problems of relatively high requirements on equipment performance, relatively low yield and content of isoquercetin and difficulty in purification in the existing pressurization preparation of isoquercetin. The semi-synthesis method of isoquercetin is characterized by comprising the following steps of 1) placing rutin in a reactor, adding water, ethyl acetate and liquid rhamnosidase, and carrying out an enzyme hydrolysis reaction to obtain a reaction solution; 2) standing and layering the reaction solution obtainedin the step 1), and collecting an ethyl acetate phase; 3) decolorizing the ethyl acetate phase obtained in the step 2); and 4) concentrating the ethyl acetate phase decolored in the step 3), standingfor cooling crystallization, and carrying out suction filtration to obtain the high-purity isoquercetin.

Description

technical field [0001] The invention belongs to the field of biosynthesis, and in particular relates to a semi-synthetic method of isoquercetin. Background technique [0002] Isoquercetin (quercetin-3-O-β-D-glucopyranoside) has good expectorant, cough, and asthma effects, and is used for the treatment of chronic bronchitis, as well as for patients with coronary heart disease and hypertension. adjuvant therapy. Isoquercetin not only has a wide range of biological activities, but also has certain advantages over quercetin and rutin in terms of safety, bioavailability and certain activities. [0003] The chemical structures of rutin, isoquercetin, and quercetin are as follows: [0004] [0005] [0006] "Enzymatically modified (α-glucosylated) isoquercetin" (enzymatically modified soquercitrin, EMIQ) is an isoquercetin derivative obtained by transglycosylation of isoquercetin with cyclodextrin glucosyltransferase , EMIQ not only has a good coloring effect, is natural a...

Claims

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Application Information

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IPC IPC(8): C12P17/06C12P19/02C07H17/07C07H3/08C07H1/06
CPCC12P17/06C12P19/02C07H17/07C07H3/08C07H1/06
Inventor 郭文华赵景辉肖金霞柏志亮
Owner SHAANXI JIAHE PHYTOCHEM
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