高等学校化学学报 ›› 2019, Vol. 40 ›› Issue (5): 909-917.doi: 10.7503/cjcu20180828

• 有机化学 • 上一篇    下一篇

含喹喔啉杨梅素衍生物的合成及生物活性

李普, 陈英, 夏榕娇, 郭涛, 张敏, 仕春, 汤旭, 贺鸣, 薛伟()   

  1. 绿色农药与农业生物工程国家重点实验室培育基地, 教育部绿色农药与生物工程重点实验室,贵州大学精细化工研究开发中心, 贵阳 550025
  • 收稿日期:2018-12-10 出版日期:2019-04-12 发布日期:2019-04-12
  • 作者简介:

    联系人简介: 薛 伟, 男, 博士, 教授, 博士生导师, 主要从事新农药创制方面的研究. E-mail: wxue@gzu.edu.cn

  • 基金资助:
    国家重点研发计划项目(批准号: 2017YFD0200506)、 国家自然科学基金(批准号: 21867003)和贵州省科技计划项目(批准号: 20185781)资助.

Synthesis and Biological Activities of Myricetin Derivatives Containing Quinoxaline

LI Pu, CHEN Ying, XIA Rongjiao, GUO Tao, ZHANG Min, JIANG Shichun, ANG Xu, HE Ming, XUE Wei*()   

  1. State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, ey Laboratory of Green Pesticide and Bioengineering of Ministry of Education, enter for Research and Development of Fine Chemicals,Guizhou University, Guiyang 550025, China
  • Received:2018-12-10 Online:2019-04-12 Published:2019-04-12
  • Contact: XUE Wei E-mail:wxue@gzu.edu.cn
  • Supported by:
    † Supported by the National Key Research and Development Program of China(No. 2017YFD0200506), the National Natural Science Foundation of China(No. 21867003) and the Science and Technology Plan Project of Guizhou Province, China(No. 20185781)

摘要:

利用活性拼接原理, 将喹喔啉引入到杨梅素结构中, 合成了一系列含喹喔啉基团的杨梅素新型衍生物. 采用浊度法测试了目标化合物的体外抑菌活性, 结果表明, 目标化合物对柑橘溃疡病菌(X. Citri)和水稻白叶枯病菌(X. Oryzae)均表现出较好的抑制活性. 目标化合物对柑橘溃疡病菌的抑制活性(EC50)均优于对照药叶枯唑和噻菌铜(EC50分别为54.85和61.13 μg/mL), 其中化合物4o抑制活性(EC50=11.17 μg/mL)最优; 目标化合物对水稻白叶枯病菌的抑制活性EC50均优于对照药叶枯唑和噻菌铜(EC50分别为148.20和175.47 μg/mL), 其中化合物4f抑制活性(EC50=34.49 μg/mL)最优. 采用半叶枯斑法测试了目标化合物的抗烟草花叶病毒(TMV)活性, 结果表明, 所有目标化合物在浓度为500 mg/L时均有一定的抑制作用.

关键词: 杨梅素, 喹喔啉, 抑菌活性, 抗烟草花叶病毒(TMV)活性

Abstract:

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 EC50 of the target compounds were superior to those of the control drugs of bismerthiazol and thiodiazole copper(54.85 and 61.13 μg/mL, respectively). Compound 4o(EC50=11.17 μg/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 μg/mL, respectively). Compound 4f(EC50=34.49 μg/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.

Key words: Myricetin, Quinoxaline, Antibacterial activity, Anti-TMV activity

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