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Pyrone compounds and preparation method and application thereof

A compound and pyrone technology, which is applied in the fields of genetic engineering and biopharmaceuticals, can solve the problems such as no antiviral activity of violapyrone compounds, and achieve the effects of low toxicity, huge market space and good activity.

Active Publication Date: 2018-06-12
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] There is no report on the antiviral activity of violapyrone compounds

Method used

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  • Pyrone compounds and preparation method and application thereof
  • Pyrone compounds and preparation method and application thereof
  • Pyrone compounds and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1: Cloning of polyketide synthase gene

[0044] 1. Genomic DNA extraction

[0045] Inoculate marine Streptomyces ZH66 in TSBY liquid medium, culture overnight at 30°C, collect the cells by centrifugation, wash with an appropriate amount of STE buffer; add 3-5 mg / ml lysozyme solution prepared by STE buffer, carefully suspend the cells, In 37°C water bath for 30min, until the cells become translucent; add 6% SDS, mix gently up and down, continue to 37°C water bath until clear; add appropriate amount of 3M NaAc (pH=4.8), then add appropriate amount of phenol:chloroform : isoamyl alcohol (25:24:1; v / v / v), mixed, and centrifuged at 12000rpm; pipette the supernatant, and repeatedly extract with phenol: chloroform: isoamyl alcohol until the middle layer is free of protein impurities, transfer to Add an equal volume of isopropanol and mix until a white flocculent DNA precipitates out; pick out the flocculent precipitate and wash it with 70% ethanol for 1-2 times; after...

Embodiment 2

[0054] Embodiment 2: Preparation of α-pyrone compound 1-4

[0055] 1. Fermentation production

[0056] (1) Cultivation of spores: According to the conventional method for cultivating microorganisms, an appropriate amount of recombinant strain I was inoculated onto MS solid slant medium and placed in a constant temperature incubator at 30° C., and cultivated for 3-4 days.

[0057] MS medium: 20g soybean powder, 20g mannitol, 20g agar powder, dissolved in water, constant volume to 1L, sterilized at 121°C for 30 minutes. After sterilization, pour the culture medium into a petri dish with a diameter of 90mm, and distribute it according to 30ml / plate.

[0058] (2) Fermentation culture

[0059] Take an appropriate amount of spores of the recombinant strain cultured on a slant for 3-4 days, inoculate them into a 250ml Erlenmeyer flask filled with 50ml of culture medium, place them on a constant temperature shaker at 30°C, and cultivate them at a speed of 220rpm for 7 days to obtain...

Embodiment 3

[0064] Example 3: Characterization of Compounds 1-4

[0065] Compound 2 Light yellow amorphous solid, UV(MeOH)(logε)λ max 290.0(3.72), molecular formula C 14 h 22 o 3 , HR-ESIMS m / z 239.1640[M+H] + . in, 1 H and 13 See Table 1 for C-NMR data.

[0066] Table 1 Compound 2 1 H and 13 C NMR data (500 and 150 MHz, in d 6 -DMSO) a

[0067]

[0068]

[0069] The signal assignments in Table 1 are based on the analysis results of H-H COZY, HMQC and HMBC spectra. The multiplicity of carbon signals is represented by s (singlet), d (doublet), t (triplet), q (quartet) and m (multiplet), respectively.

[0070] Compound 1 is a light yellow amorphous solid, molecular formula C 13 h 20 o 3 , HR-ESIMS m / z 225.1483[M+H] + .

[0071] Compound 3 is light yellow amorphous solid, molecular formula C 14 h 22 o 3 , HR-ESIMS m / z 239.1640[M+H] + .

[0072] Compound 4 is light yellow amorphous solid, molecular formula C 14 h 22 o 3 , HR-ESIMS m / z 239.1638[M+H] + .

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Abstract

The invention provides alpha-pyrone compounds having antiviral activity and their application in resisting influenza viruses H1N1 and H3N2. The invention also discloses a preparation method of the alpha-pyrone compounds having antiviral activity, comprising: (1) acquiring a fermented material having rich pyrone compounds through microbial fermentation culture, wherein a recombinant vector used inthe microbial fermentation culture carries polyketide synthase having a nucleotide sequence of KU534995.1; (2) separating and purifying the fermented material of step (1) to obtain the alpha-pyrone compounds. Compared with existing drugs, the pyrone compounds have good anti-H2N1 and anti-H3N2 activity and are substantially nontoxic to normal cells; compared with existing drugs, the alpha-pyrone compounds have natural advantages, including good activity and toxic and side effects reduced as far as possible, and also have a promising application prospect and huge market.

Description

technical field [0001] The invention belongs to the technical fields of genetic engineering and biopharmaceuticals, and in particular relates to a method for producing pyrone compounds with recombinant bacterial strains; the invention also relates to the application of the compounds in anti-influenza virus. Background technique [0002] Influenza (abbreviated as "flu") is an acute respiratory infection caused by influenza virus, and it is also a highly contagious and fast-spreading disease. Influenza spreads mainly through airborne droplets, person-to-person contact, or contact with contaminated items. Typical clinical symptoms are: sudden onset of high fever, general pain, significant fatigue and mild respiratory symptoms. Generally, autumn and winter are the high-incidence period, and the complications and death caused by it are very serious. The disease is caused by influenza virus, which can be divided into three types: A (A), B (B), and C (C). Type A virus often under...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/38A61K31/366A61P31/16C12N15/63C12N15/52
CPCC07D309/38C12N9/00
Inventor 李文利侯路宽李花月黄会明
Owner OCEAN UNIV OF CHINA
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