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2-quinolinone-citrinin hybrid dimer compound as well as preparation method and application thereof

A technology of quinolinone and citrinin, which is applied in the field of natural small molecule drugs, can solve the problem that the activity needs to be further developed

Active Publication Date: 2022-06-03
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the activity of such compounds needs to be further developed

Method used

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  • 2-quinolinone-citrinin hybrid dimer compound as well as preparation method and application thereof
  • 2-quinolinone-citrinin hybrid dimer compound as well as preparation method and application thereof
  • 2-quinolinone-citrinin hybrid dimer compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Example 1: Isolation of 2-quinolinone-citrinin hybrid dimer compound

[0040] (1) Strain: Penicillium sp. GGF16-1-2GDMCC No: 61080.

[0041] PDA medium: potato 200g, glucose 20g, sea salt 35g, pure water 1L, pH natural;

[0042] Liquid medium: 1L, maltose 40g, tryptophan 5g, sorbitol 50g, monosodium glutamate 10g, KH2 PO 4 5g, MgSO 4 ·7H 2 O 3g, yeast extract 13g, balance of old seawater, pH 6.5.

[0043] (2) Activation of strains: Use an inoculating loop to pick strains from the strain tube into a culture flask (100mL / 250mL) containing PDA medium, and place it on a constant temperature shaker (165r / min) at 28°C. Cultivated in medium for 2 days to obtain seed liquid.

[0044] (3) Inoculation: suck 1.5 mL of the activated seed culture solution into a 1000 mL culture flask containing 400 mL of liquid medium, and place it in a room at 28° C. for static culture for 60 days, with a total of 150 L of culture.

[0045] (4) Extraction: add 10-20 mL of methanol to each of ...

Embodiment 2

[0048] Example 2: Identification of 2-quinolinone-citrinin hybrid dimer compounds

[0049] (1) Compound I, orange-yellow amorphous powder, quasi-molecular ion peak m / z given by positive ion HRESIMS: 394.1647 [M+H] + (Calculated m / z: 394.1649[M+H] + ), determine its molecular formula as C 23 H 23 NO 5 , the desaturation is 13. The maximum absorption wavelengths shown in the ultraviolet spectrum are: 220nm, 286nm and 320nm. Infrared spectrum shows carbonyl (1722cm -1 , 1635cm -1 ) and benzene ring (1608cm -1 , 1519cm -1 , 1494cm -1 and 1457cm -1 ) group.

[0050] 1 H and 13 The results of the C NMR spectrum showed that most of the signals were in pairs and in a 1:1 ratio, probably due to 3 The presence of intramolecular hydrogen bonds in the solvent causes its rotation to be hindered, resulting in two sets of spectra. 1 The H NMR spectrum shows 4 aromatic proton signals δ H 7.27(1H,t,7.6,2.0Hz,H-7), 7.35(1H,d,8.0Hz,H-9), 7.55(1H,t,7.2,1.2Hz,H-8), 8.16(1H, d,8.0...

Embodiment 3

[0071] Example 3: Antibacterial performance test of 2-quinolinone-citrinin hybrid dimer compound:

[0072] Since there is only an antibacterial performance test, the present invention will simultaneously apply for the protection compound and its application, which should be fully disclosed and characterized for a variety of antibacterial properties, so as to expand its application range. It can be considered to adopt a variety of strains including positive bacteria and Negative bacteria were tested.

[0073] (1) Mycelial growth rate method: prepare compound liquids of different concentrations (repeated 3 times for each concentration), pour them into petri dishes for later use, and use the PDA medium plate with sterile water as a control. Take the cultured pathogenic bacteria cake (Staphylococcus epidermidis, Staphylococcus aureus, Methicillin-resistant Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa provided by Guangdong Microorganisms) with a sterile hole p...

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Abstract

The invention belongs to the technical field of natural polymers, and particularly relates to a 2-quinolinone-citrinin hybrid dimer compound as well as a preparation method and application thereof. One monomer 4-hydroxy-1-methyl quinoline-2-ketone alkaloid in the 2-quinolinone-citrinin hybrid dimer compound disclosed by the invention is mainly obtained from actinomycetes Dactylosporangium sp. Of plants such as rutaceae and euphorbiaceae at present, and actinomycetes Dactylosporangium sp. Of soil sources are mainly obtained from actinomycetes Dactylosporangium sp. Of plants such as the rutaceae and the euphorbiaceae at present. The compound has wide biological activity, such as anti-platelet aggregation, chymotrypsin inhibition, anti-tumor activity, antibacterial activity, anti-tuberculosis activity and the like. The method can be applied to the field of antibacterial drug preparation.

Description

technical field [0001] The invention belongs to the technical field of natural small molecule medicines, in particular to a class of 2-quinolinone-citrinin hybrid dimer compounds and a preparation method and application thereof. Background technique [0002] 2-Quinolinones are a class of biologically active compounds with a wide range of effects. Since the 1970s and 1980s, scholars at home and abroad have carried out extensive research on the synthesis of quinolinones, which are mainly developed as anticonvulsant, analgesic, hypnotic and other central system inhibitory drugs. Natural 2-quinolinone alkaloids are mainly derived from plants, and there are also reports in animals, such as Chinese medicine dung beetle (compound 1-5), white fresh skin (compound 6-14), Chinese prickly ash (compound 15-21) and other traditional Chinese medicines. , as shown in the following formula (1). The alkaloids derived from dung beetles are basically the same as the natural coumarin, except ...

Claims

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Application Information

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IPC IPC(8): C07D405/06A61K31/4709A61P31/00A61P31/04A01N43/42A01P3/00C12P17/16C12R1/80
CPCC07D405/06A61K31/4709A61P31/00A61P31/04A01N43/42C12P17/16Y02A50/30
Inventor 张翠仙胡金姗邵雪花冯婵韦霞李小翚张琪
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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