Synthesis and Biological Activities of Myricetin Derivatives Containing Quinoxaline

被引:11
作者
Li Pu [1 ]
Chen Ying [1 ]
Xia Rongjiao [1 ]
Guo Tao [1 ]
Zhang Min [1 ]
Jiang Shichun [1 ]
Tang Xu [1 ]
He Ming [1 ]
Xue Wei [1 ]
机构
[1] Guizhou Univ, State Key Lab Breeding Base Green Pesticide & Agr, Ctr Res & Dev Fine Chem, Key Lab Green Pesticide & Bioengn,Minist Educ, Guiyang 550025, Guizhou, Peoples R China
来源
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE | 2019年 / 40卷 / 05期
基金
中国国家自然科学基金;
关键词
Myricetin; Quinoxaline; Antibacterial activity; Anti-TMV activity; ANTIBACTERIAL ACTIVITY; SULFONE DERIVATIVES; INHIBITION; DESIGN;
D O I
10.7503/cjcu20180828
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
According to the active substructure combination theory, a series of novel myricetin derivatives containing quinoxaline moieties was synthesized by introducing the quinoxaline blocks into the structures of myricetins. The antibacterial activities of the target compounds were evaluated via turbidimeter test in vitro. The preliminary bioassay results indicated that all of the title compounds exhibited certain antibacterial activities in vitro against Xanthomonas axonopodis pv. Citri (X. citri) and Xanthomonas oryzae pv. Oryzae (X. oryzae) . The compounds were also tested to evaluate the half maximal effective concentration (EC50) of phytopathogenic bacteria. The results showed that all the X. citri ECof the target compounds were superior to those of the control drugs of bismerthiazol and thiodiazole copper(54. 85 and 61. 13 mu g/mL, respectively) . Compound 4o (EC50 = 11. 17 mu g/mL) exhibited the best activity. All of the X. oryzae EC50 of the target compounds were superior to the control drugs of bismerthiazol and thiodiazole copper (148. 20 and 175. 47 mu g/mL , respectively) . Compound 4f(EC50= 34. 49 mu g/mL) exhibited the best activity. The in vivo efficacies against tobacco mosaic virus (TMV) of the target compounds were tested through half-leaf method. The results of bioassay showed that the target compounds exhibited certain anti-TMV activities at the concentration of 500 mg/L.
引用
收藏
页码:909 / 917
页数:9
相关论文
共 23 条
[11]   Improvement of insulin sensitivity in obese Zucker rats by myricetin extracted from Abelmoschus moschatus [J].
Liu, I-Min ;
Tzeng, Thing-Fong ;
Liou, Shorong-Shii ;
Lan, Ting-Wei .
PLANTA MEDICA, 2007, 73 (10) :1054-1060
[12]   Design, synthesis and biological evaluation of (E)-2-(2-arylhydrazinyl) quinoxalines, a promising and potent new class of anticancer agents [J].
Rodrigues, Felipe A. R. ;
Bomfim, Igor da S. ;
Cavalcanti, Bruno C. ;
Pessoa, Claudia do O. ;
Wardell, James L. ;
Wardell, Solange M. S. V. ;
Pinheiro, Alessandra C. ;
Kaiser, Carlos Roland ;
Nogueira, Thais C. M. ;
Low, John N. ;
Gomes, Ligia R. ;
de Souza, Marcus V. N. .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2014, 24 (03) :934-939
[13]   Syntheses and Bioactivities of Myricetin Derivatives Containing Piperazine Acidamide Moiety [J].
Ruan Xianghui ;
Zhao Hongju ;
Zhang Cheng ;
Chen Lijuan ;
Li Pu ;
Wang Yihui ;
He Ming ;
Xue Wei .
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2018, 39 (06) :1197-1204
[14]   Three distinct neuroprotective functions of myricetin against glutamate-induced neuronal cell death: Involvement of direct inhibition of caspase-3 [J].
Shimmyo, Yoshiari ;
Kihara, Takeshi ;
Akaike, Akinori ;
Niidome, Tetsuhiro ;
Sugimoto, Hachiro .
JOURNAL OF NEUROSCIENCE RESEARCH, 2008, 86 (08) :1836-1845
[15]   Naturally Occurring Flavonoids Against Human Norovirus Surrogates [J].
Su, Xiaowei ;
D'Souza, Doris H. .
FOOD AND ENVIRONMENTAL VIROLOGY, 2013, 5 (02) :97-102
[16]  
Suguna M., 2010, Journal of Chemical and Pharmaceutical Research, V2, P7
[17]   Synthesis and Antibacterial Activities of Myricetin Derivatives Containing Acidamide Moiety [J].
Xiao Wei ;
Ruan Xianghui ;
Li Qin ;
Zhang Juping ;
Zhong Xinmin ;
Xie Yan ;
Wang Xiaobin ;
Huang Minguo ;
Xue Wei .
CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2017, 38 (01) :35-40
[18]   Synthesis and Antibacterial Activity of Oxazolidinone Derivatives Containing Nitro Heteroaromatic Moiety [J].
Xu Boxuan ;
Ding Xiudong ;
Wu Yachuang ;
Cui Lei ;
Qian Ping ;
Wang Di ;
Zhao Yanfang .
CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2018, 34 (01) :51-56
[19]   Inhibition of Tobacco Bacterial Wilt with Sulfone Derivatives Containing an 1,3,4-Oxadiazole Moiety [J].
Xu, Wei-Ming ;
Han, Fei-Fei ;
He, Ming ;
Hu, De-Yu ;
He, Jiang ;
Yang, Song ;
Song, Bao-An .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2012, 60 (04) :1036-1041
[20]   Novel myricetin derivatives: Design, synthesis and anticancer activity [J].
Xue, Wei ;
Song, Bao-An ;
Zhao, Hong Ju ;
Qi, Xing Bao ;
Huang, Yin Jiu ;
Liu, Xin Hua .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2015, 97 :155-163