Piperonyl-Tethered Rhodanine Derivatives Potently Inhibit Chitinolytic Enzymes of Ostrinia furnacalis .
Qing HanNan WuYao-Yang LiuJing-Yu ZhangRu-Lei ZhangHui-Lin LiZhi-Yang JiangJia-Xing HuangHong-Xia DuanQing YangPublished in: Journal of agricultural and food chemistry (2022)
Insect pest chitinases are potential target for developing new insect growth regulators. Piperine was found first to inhibit the insect chitinase ( Of Chi-h) from Ostrinia furnacalis (Asian corn borer) in this work, except for previously reported Of ChtI. 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 Of ChtI and Of Chi-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 π 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.