Piperonyl-Tethered Rhodanine Derivatives Potently Inhibit Chitinolytic Enzymes of Ostrinia furnacalis

文献类型： 外文期刊

第一作者： Han, Qing

作者： Han, Qing;Liu, Yao-Yang;Zhang, Jing-Yu;Zhang, Ru-Lei;Li, Hui-Lin;Jiang, Zhi-Yang;Huang, Jia-Xing;Duan, Hong-Xia;Wu, Nan;Yang, Qing;Yang, Qing;Yang, Qing

作者机构：

关键词： piperonyl-tethered rhodanine derivatives; chitinase; chitinase inhibitor; insect growth and regulator; pesticide

期刊名称：JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY （ 影响因子：5.895； 五年影响因子：6.048 ）

ISSN： 0021-8561

年卷期： 2022 年 70 卷 24 期

页码：

收录情况： SCI

摘要： Insect pest chitinases are potential target for developing new insect growth regulators. Piperine was found first to inhibit the insect chitinase (OfChi-h) from Ostrinia furnacalis (Asian corn borer) in this work, except for previously reported OfChtI. Novel piperonyl-tethered rhodanine derivatives 7a-j were rationally designed with piperine as lead and synthesized by introducing a unique rhodanine moiety into the piperine scaffold based on the similar binding cavity of OfChtI and OfChi-h. Compared to piperine, compounds 7a-j showed approximately 100- to 400-fold or 110- to 210-fold higher inhibitory capacity against two chitinases, respectively. Molecular mechanism studies indicated that pi interactions are crucial for improving inhibitory activity against two chitinases due to the introduction of the conjugated rhodanine ring. Moreover, compounds 7a-c could dramatically inhibit the growth and development of O. furnacalis larvae by in vivo activity evaluation. This study provides novel piperonyl-tethered rhodanine derivatives inhibiting dual chitinases as insect growth regulator candidates.

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