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Antiviral compound containing luteolin and preparation method thereof

A kind of luteolin and antiviral technology, applied in the direction of antiviral agent, organic chemistry, etc., to achieve the effect of low cost and simple production

Active Publication Date: 2020-11-27
XIAMEN 139 BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few studies on the preparation of luteolin-quercetin or luteolin-luteolin compounds at home and abroad.

Method used

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  • Antiviral compound containing luteolin and preparation method thereof
  • Antiviral compound containing luteolin and preparation method thereof
  • Antiviral compound containing luteolin and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Preparation of antiviral luteolin-quercetin compound:

[0039] Step a: Dissolve NBS in acetone and stir to dissolve it at room temperature and avoid light; dissolve luteolin in acetone, add BPO, slowly add the acetone solution of NBS in an ice bath, and heat to 80°C, reacted for 18 hours, after the reaction was over, distilled under reduced pressure, evaporated acetone, washed with deionized water several times and freeze-dried to obtain 8-bromoluteolin, wherein n(luteolin):n(NBS )=1:1.5, m(BPO):m(luteolin)=5%;

[0040]Step b: Dissolve borax, 8-bromoluteolin and quercetin in water respectively in two three-necked flasks, and stir at room temperature for 1 hour to obtain 8-bromoluteolin boronic acid complex and quercetin boronic acid complex , wherein the molar ratio of n (8-bromoluteolin) to n (borax) is 7:1, and the molar ratio of n (quercetin) to n (borax) is 6:1;

[0041] Step c: Add 8-bromoluteolin boronic acid complex, quercetin boronic acid complex, N-methylpyrr...

Embodiment 2

[0043] Preparation of antiviral luteolin-quercetin compound:

[0044] Step a: Dissolve NBS in acetone and stir to dissolve it at room temperature and avoid light; dissolve luteolin in acetone, add BPO, slowly add the acetone solution of NBS in an ice bath, and heat to 70°C, reacted for 12 hours, after the reaction was over, distilled under reduced pressure, evaporated acetone, washed with deionized water several times and freeze-dried to obtain 8-bromoluteolin, wherein n(luteolin):n(NBS )=1:1.1, m(BPO):m(luteolin)=4%;

[0045] Step b: Dissolve borax, 8-bromoluteolin and quercetin in water respectively in two three-necked flasks, and stir at room temperature for 1 hour to obtain 8-bromoluteolin boronic acid complex and quercetin boronic acid complex , wherein the molar ratio of n (8-bromoluteolin) to n (borax) is 5:1, and the molar ratio of n (quercetin) to n (borax) is 4:1;

[0046] Step c: Add 8-bromoluteolin boronic acid complex, quercetin boronic acid complex, N-methylpyr...

Embodiment 3

[0050] Preparation of antiviral luteolin-quercetin compound:

[0051] Step a: Dissolve NBS in acetone and stir to dissolve it at room temperature and avoid light; dissolve luteolin in acetone, add BPO, slowly add the acetone solution of NBS in an ice bath, and heat to 50°C, reacted for 9 hours, after the reaction was over, distilled under reduced pressure, evaporated acetone, washed several times with deionized water and freeze-dried to obtain 8-bromoluteolin, wherein n(luteolin):n(NBS )=1:1.1, m(BPO):m(luteolin)=2%;

[0052] Step b: Dissolve borax, 8-bromoluteolin and quercetin in water respectively in two three-necked flasks, and stir at room temperature for 1 hour to obtain 8-bromoluteolin boronic acid complex and quercetin boronic acid complex , wherein the molar ratio of n (8-bromoluteolin) to n (borax) is 3:1, and the molar ratio of n (quercetin) to n (borax) is 2:1;

[0053] Step c: Add 8-bromoluteolin boronic acid complex, quercetin boronic acid complex, N-methylpyrr...

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Abstract

The invention discloses an antiviral compound containing luteolin and a preparation method thereof. The method comprises the following steps: taking luteolin and quercetin as raw materials, carrying out free radical reaction, carrying out C-O coupling reaction, firstly, carrying out reaction by utilizing N-bromosuccinimide and luteolin, taking dibenzoyl peroxide as a reaction initiator and synthesizing the 8-bromoluteolin; then, protecting quercetin, luteolin and 8-bromoluteolin through borax; and by taking cuprous chloride or cuprous iodide as a catalyst, 2,2,6,6-tetramethyl-3,5-heptanedioneor 1,10-phenanthroline as a ligand and cesium carbonate as an alkali, carrying out reacting under the protection of nitrogen, and deprotecting by using hydrochloric acid after the reaction is finishedto obtain the product antiviral luteolin-quercetin or antiviral luteolin-luteolin compound. The process is simple in production and low in cost, and industrial large-scale production of the antiviralluteolin-quercetin and the antiviral luteolin-luteolin compound is facilitated.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and specifically relates to a luteolin-containing antiviral compound and a preparation method thereof. Background technique [0002] Edible fungi are a kind of healthy food. They are rich in nutrients such as vitamins, minerals, proteins, polysaccharides and flavonoids, so they have high edible and application value, and they are low in fat and calories. Grifola frondosa ( Grifola frondosa ), also known as Polyporus bayae, is an edible fungus with a wide range of sources. Its mature fruiting bodies are dark gray-brown in flesh, and the color gradually becomes light gray afterward. Various chemical active ingredients such as flavonoids, polysaccharides, organic acids, alkaloids, coumarins, steroids and triterpenes can be isolated and purified from Grifola frondosa. These active ingredients have the functions of lowering blood fat, blood sugar, Moisturizing the lungs, protecting the liver, an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/30A61P31/12
CPCC07D311/30A61P31/12Y02A50/30
Inventor 刘斌葛小东陈颖
Owner XIAMEN 139 BIOTECH CO LTD
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