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Sclerotiorin derivatives and their preparation methods and their application as anti-h1n1 influenza virus agents

A technology of derivatives and type A, applied in the field of sclerotiorin derivatives and their preparation, can solve the problems that no natural compound or its derivatives have anti-type A H1N1 influenza virus agents, etc., achieve strong inhibitory activity and broad application prospects Effect

Active Publication Date: 2017-12-12
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of natural compounds or their derivatives directly from marine microorganisms as anti-H1N1 influenza virus agents has not been seen in recent years.

Method used

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  • Sclerotiorin derivatives and their preparation methods and their application as anti-h1n1 influenza virus agents
  • Sclerotiorin derivatives and their preparation methods and their application as anti-h1n1 influenza virus agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] (1) The culture of the endophytic fungus Penicillium sp. (TA33-1) of Gorgonian coral

[0014] The culture medium used for strain culture contains glucose 1.0% (percentage by weight, the same below), yeast extract 0.2%, peptone 0.2%, agar 1.0%, sodium chloride 3.0%, and the rest is water. Strains were cultured at 30°C for 3 days.

[0015] (2) Fermentation of the endophytic fungus Penicillium sp. (TA33-1) from Gorgonian coral

[0016] The culture medium used in the fermentation culture contains 40.0% rice (percentage by weight, the same below), 3.0% sodium chloride, and the rest is water; the fungal strain is cultured at 28° C. for 30 days.

[0017] (3) Extraction and separation of (+)-Sclerotiorin

[0018] Get 60 bottles of mycelia obtained in step (2), extract 3 times with chloroform-methanol mixed solution (1:1) and concentrate under reduced pressure, then extract 3 times with ethyl acetate to obtain crude extract; Extraction extract is carried out normal phase sili...

Embodiment 2

[0020] (1) The culture of the endophytic fungus Penicillium sp. (TA33-1) of Gorgonian coral

[0021] The culture medium used for strain cultivation contains 0.1%-5.0% of glucose (percentage by weight, the same below), 0.01%-1% of yeast extract, 0.01%-1% of peptone, 0.1%-3.0% of agar, and 0.05% of sodium chloride- 5%, and the rest is water. When used, it is made into a test tube slant, and the fungal strains are cultivated at 0-30°C for 3-15 days.

[0022] (2) Fermentation of the endophytic fungus Penicillium sp. (TA33-1) from Gorgonian coral

[0023] The culture medium used in the fermentation culture contains 1.0%-80.0% (weight percentage, the same below) of rice, 0.05%-5% of sodium chloride and the rest is water, and the fungal strain is cultivated at 0-30°C for 10-60 days.

[0024] (3) Extraction and separation of (+)-Sclerotiorin compound

[0025] Take 10-300 bottles of the obtained mycelium obtained in step (2), extract the obtained mycelium with chloroform-methanol mix...

Embodiment 3

[0028] Weigh the dried (+)-Sclerotiorin (0.1mol) and dissolve it in dichloromethane. Under normal temperature, add the organic primary amine (0.12mol) dropwise to the reaction solution under full stirring, and react for 1 hour Finally, add distilled water (200mL) to the reactant to terminate the reaction, extract with ethyl acetate (500mL), concentrate the extract, perform column chromatography, elute with ethyl acetate, concentrate the eluate, and recrystallize After obtaining the compound of formula I.

[0029] Other organic chemical reaction conditions not specifically specified in Example 3, and other experimental operating conditions such as normal phase silica gel column chromatography separation are all conventional experimental operating conditions in this field, and those skilled in the art can make reasonable choices according to actual needs .

[0030] Specific compound structure examples of compounds of formula I:

[0031]

[0032] The structural confirmation ...

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Abstract

A sclerotiorin derivative and a preparation method and an application thereof as an anti-influenza A (H1N1) virus agent are provided. The preparation method comprises the steps: during preparation, firstly, carrying out strain cultivation on fungi penicillium sp. (TA33-1), then carrying out fermentation cultivation on the fungi, leaching the obtained mycelia with a chloroform-methanol mixed liquid (1:1) for three times, carrying out reduced pressure concentration, and extracting for three times with ethyl acetate to obtain a crude extract; and successively carrying on positive-phase silica gel column chromatography, Sephadex LH-20 gel column chromatography and HPLC high performance liquid chromatography, to obtain a yellow powder, namely (+)-sclerotiorin; and adding organic primary amine and potassium carbonate in a dichloromethane dissolved with (+)-sclerotiorin, and carrying out a reaction to obtain a compound represented by the formula I. The invention provides the anti-influenza A (H1N1) virus agent, and is characterized in that the compound represented by the formula I or a pharmaceutical acceptable salt thereof is used in treatment of influenza caused by influenza A (H1N1) virus.

Description

technical field [0001] The invention relates to a sclerotiorin derivative and its preparation method and application, in particular to a sclerotiorin derivative with strong inhibitory activity against influenza A (H1N1) virus, its preparation method and application. Background technique [0002] Influenza A (H1N1) virus is a type A influenza virus that carries H1N1 subtype swine influenza virus strains, including ribonucleic acid gene fragments of three influenza viruses: avian influenza, swine influenza and human influenza, as well as Asian swine influenza and African swine influenza Influenza virus characteristics. Since the outbreak of H1N1 influenza virus in Mexico on March 18, 2009, cases of infection and death have been found successively. Therefore, finding a safe and efficient anti-H1N1 influenza virus agent has become an urgent problem in the world. Marine natural products are considered an important source of novel antiviral agents. Marine microorganisms have be...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/04C07D401/04A61K31/472A61K31/4725A61P31/16C12P17/12C12P17/16C12R1/80
CPCC07D217/04C07D401/04C12P17/12C12P17/165
Inventor 邵长伦王长云魏美燕胥汝芳管菲菲
Owner OCEAN UNIV OF CHINA
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