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Synthesis And Biological Activity Of Myricetin Derivatives Containing Oxadiazole Sulfid

Posted on:2023-12-21Degree:MasterType:Thesis
Country:ChinaCandidate:F PengFull Text:PDF
GTID:2531306785963299Subject:Pesticides
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Myricetin,a flavonoid,belongs to polyphenols,which has a wide range of significant biological activities such as antiviral,antibacterial,anticancer and antiproliferative.1,3,4-oxadiazole thioether is one of the important five-membered nitrogen-containing heterocyclic compounds.1,3,4-oxadiazole thioether is a small molecule compound with active group,and its biological activity is remarkable in antibacterial,antiviral,antifungal,insecticidal and other aspects,and plays an important role in the creation of pesticides.In this paper,the active group containing1,3,4-oxadiazole thioether was introduced into the lead compound myricetin,and three types of myricetin derivatives containing 1,3,4-oxadiazole thioether were synthesized.All target compounds were characterized by 1H NMR,13C NMR and HRMS.The crystal structure of A8 was determined by single crystal ray diffractometer.Simultaneously,the biological activities of the target compounds against phytopathogens and antiviral were tested.The turbidimetric method was adopted to detect the antibacterial effects of the target compounds.The results showed that the EC50values of A12,C23 and C26against Xac were 42.2,28.0 and 40.7μg/mL,respectively,which preceded the lead compound myricetin(135.6μg/mL),control agent BT(79.8μg/mL)and TC(98.7μg/mL).Meanwhile,the EC50values of A12,A16,A24,C23,C24,C26 and C32against Psa were 48.3,41.2,30.7,38.8,41.8,22.5 and 32.8μg/mL,respectively,which surpassed myricetin(291.6μg/mL),control agent BT(105.3μg/mL)and TC(140.9μg/mL).Furthermore,the EC50values of A6,A8,C24,and C26 against Xoo were 32.4,19.7,30.4 and 15.3μg/mL,respectively,which were superior to the lead compound myricetin(122.5μg/mL),control agent BT(73.9μg/mL)and TC(98.8μg/mL).The mechanism of A8 and C26 on Xoo and C26 on Psa was further studied by SEM.It was found that the cells in the group that had not been treated with drugs were uniform in size and complete in shape.A part of the cell membranes was flattened and not completely ruptured at 50μg/mL.Note that at 100μg/mL,cell ruptures increased significantly.The half leaf spot method was used to test the anti-TMV activity of the target compounds,and ningnanmycin was used as a control drug.The results showed that the EC50values of the anti-TMV curative activities of A9,C16,C26,E12,E17 and E19 were 195.2,183.5,131.6,128.8,183.4 and 136.3μg/mL,better than ningnamycin(296.4μg/mL).In addition,the EC50values of the anti-TMV protective activities of A9,C16,C26,E12,E17 and E19 were 189.9,149.0,101.3,99.1,151.7and 119.3μg/mL,better than ningnamycin(307.6μg/mL).The interactions between A9,A13,C16,C26,E12,E19,myricetin,ningnamycin and tobacco mosaic virus coat protein(TMV CP)were further investigated by microcalorimetry(MST).The Kdvalues of A9,A13,C16,C26,E12,E19 and TMV CP were 0.003±0.001,0.256±0.071,0.378±0.163,0.038±0.011,0.029±0.013,0.069±0.028μmol/L,respectively,which were better than myricetin(31.531±2.445μmol/L)and ningnanmycin(2.726±1.301μmol/L).It showed that the binding ability of A9,A13,C16,C26,E12 and E19 was stronger than that of myricetin and ningnanmycin.
Keywords/Search Tags:myricetin, oxadiazole thioether, sulfonate(carboxylate), biological activity, mechanism of action
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