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Diketopiperazine compound as well as preparation and application thereof

A technology of diketopiperazines and compounds, applied in the field of diketopiperazines and their preparation, capable of solving biological and human health hazards, water and soil pollution, etc.

Active Publication Date: 2018-08-31
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In recent years, with the development of aquaculture scale and the extensive use of traditional antibiotics in the aquaculture process, multi-drug resistance of pathogenic bacteria in aquaculture animals and bacteria in the aquaculture environment has become increasingly common, and the extensive use of chemically synthesized drugs has negative effects on water bodies and soils. It has brought serious pollution, which has caused direct and potential harm to organisms and human health.

Method used

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  • Diketopiperazine compound as well as preparation and application thereof
  • Diketopiperazine compound as well as preparation and application thereof
  • Diketopiperazine compound as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The structure of the diketopiperazine compound derived from the endophytic fungus of seaweed is shown in formula (I).

[0025]

[0026] The compound has the following physicochemical and spectroscopic properties:

[0027] Colorless oil; specific rotation [α] 22 D -81(c 0.050, MeOH); H NMR spectrum (solvent is deuterated methanol) δ H 5.24d(5.0), 2.05dt(13.2,3.3), 1.91m, 2.15m, 2.15m, 4.26t(8.8), 4.09dd(8.1,4.0), 1.93m, 1.52m, 1.89m, 0.99d(6.4 ), 0.97d(6.3), 3.37s; C NMR spectrum (solvent is deuterated chloroform) δ C 171.1(C), 88.5(CH), 31.8(CH 2 ), 25.3 (CH 2 ), 60.5(CH), 173.6(C), 55.0(CH), 38.8(CH 2 ),25.9(CH),23.4(CH 3 ),22.0(CH 3 ), 57.4 (CH 3 ); high-resolution mass spectrometry [M] + m / z 240.1488, calculated 240.1474.

Embodiment 2

[0029] The preparation method of diketopiperazine compound as shown in formula (I):

[0030] Take Trichoderma asperellum cf44-2 (Trichoderma asperellumcf44-2) bacterial classification that grows well on the plate, cut into small pieces and inoculate in potato dextrose liquid medium, put 300 milliliters of culture medium in every 1 liter of Erlenmeyer flasks, totally 200 bottle, and fermented at room temperature for 30 days, and then the fermentation product was extracted three times with ethyl acetate, concentrated under reduced pressure, and 83.7 grams of crude extract were obtained after concentration.

[0031] The potato glucose liquid medium consists of 500 milliliters of boiled juice containing 200 grams of potatoes per liter, 20 grams of glucose, 5 grams of peptone, 5 grams of yeast powder, and 500 milliliters of aged seawater.

[0032] Trichoderma asperellum cf44-2 (Trichoderma asperellum cf44-2) strain was preserved in China Center for Type Culture Collection CCTCC on ...

Embodiment 3

[0037] The difference from Example 2 is that

[0038] Get the Trichoderma asperellum cf44-2 (Trichoderma asperellum cf44-2) bacterial classification that grows well on the plate, cut into small pieces and inoculate in Jerusalem artichoke glucose liquid medium, put 300 milliliters of culture medium in every 1 liter of Erlenmeyer flasks, altogether 200 bottles, fermented at room temperature for 40 days, then extracted three times with dichloromethane, concentrated under reduced pressure, and obtained 80 grams of crude extract after concentration.

[0039] The Jerusalem artichoke glucose liquid medium consists of 500 milliliters of boiled juice containing 200 grams of Jerusalem artichoke tubers per liter, 20 grams of glucose, 5 grams of peptone, 5 grams of yeast powder, and 500 milliliters of aged sea water.

[0040] The crude extract was subjected to 200-300 mesh silica gel column chromatography, followed by volume ratios of 50:1, 30:1, 15:1, 10:1, 5:1, 2:1, 1:1 to 0:1 Carry ou...

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Abstract

The invention relates to the field of antibacterial agents and in particular discloses a diketopiperazine compound derived from alga endophytic fungi, as well as a preparation method and application thereof in preventing bacteria. The compound is of a specific structure formula of formula (I) as shown in the specification. The preparation method comprises the following steps: inoculating Trichoderma asperellum cf44-2 into a fungus culture medium, performing fermentation culture, and separating and purifying a fermentation product, thereby obtaining the diketopiperazine compound of formula (I)as shown in the specification. Antibacterial activity experiments of the diketopiperazine compound disclosed by the invention show that the diameter of an antibacterial ring of the compound of a dosage of 20 microgramme / tablet can be up to 6.5 millimeters.

Description

technical field [0001] The invention relates to the field of antibacterial agents, in particular to a diketopiperazine compound derived from seaweed endophytic fungi, a preparation method thereof and an application in antibacterial aspects. Background technique [0002] The aquaculture industry occupies an important proportion in the national economy. At present, there are various types of aquaculture, but almost all of them are threatened by diseases. The frequent occurrence of aquaculture diseases not only causes significant economic losses, but also lays hidden dangers for the quality and safety of aquatic products. According to the monitoring results of aquaculture animal diseases, there are more than 200 kinds of aquaculture diseases in recent years, of which bacterial diseases account for more than 48%. Among bacterial aquatic animal diseases, vibriosis caused by Vibrio bacteria is the most important bacterial disease. The disease has a wide range of occurrence, high ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P31/04C12P17/18C12R1/885
CPCA61P31/04C07D487/04C12P17/182
Inventor 季乃云宋银平
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI