Diversity-Oriented Synthesis of Natural-Product-like Libraries Containing a 3-Methylbenzofuran Moiety for the Discovery of New Chemical Elicitors.
Natural products are a major source of biological molecules. The 3-methylfuran scaffold is found in a variety of plant secondary metabolite chemical elicitors that confer host-plant resistance against insect pests. Herein, the diversity-oriented synthesis of a natural-product-like library is reported, in which the 3-methylfuran core is fused in an angular attachment to six common natural product scaffolds-coumarin, chalcone, flavone, flavonol, isoflavone and isoquinolinone. The structural diversity of this library is assessed computationally using cheminformatic analysis. Phenotypic high-throughput screening of β-glucuronidase activity uncovers several hits. Further in vivo screening confirms that these hits can induce resistance in rice to nymphs of the brown planthopperNilaparvata lugens. This work validates the combination of diversity-oriented synthesis and high-throughput screening of β-glucuronidase activity as a strategy for discovering new chemical elicitors.
Department of Chemistry Zhejiang University Hangzhou 310027 P. R. China.
Xingrui
X
He
State Key Laboratory of Rice Biology Institute of Insect Science Zhejiang University Hangzhou 310058 P. R. China.
Xia
X
Chen
Department of Chemistry Zhejiang University Hangzhou 310027 P. R. China.
Songbo
S
Lin
State Key Laboratory of Rice Biology Institute of Insect Science Zhejiang University Hangzhou 310058 P. R. China.
Xiaochang
X
Mo
State Key Laboratory of Rice Biology Institute of Insect Science Zhejiang University Hangzhou 310058 P. R. China.
Pengyong
P
Zhou
Department of Chemistry Zhejiang University Hangzhou 310027 P. R. China.
Zhihao
Z
Zhang
School of Biological and Chemical Engineering Zhejiang University of Science and Technology Hangzhou 310023 P. R. China.
Yaoyao
Y
Lu
School of Biological and Chemical Engineering Zhejiang University of Science and Technology Hangzhou 310023 P. R. China.
Yu
Y
Yang
Department of Chemistry Zhejiang University Hangzhou 310027 P. R. China.
Haining
H
Gu
Department of Chemistry Zhejiang University Hangzhou 310027 P. R. China.
Zhicai
Z
Shang
State Key Laboratory of Rice Biology Institute of Insect Science Zhejiang University Hangzhou 310058 P. R. China.
Yonggen
Y
Lou
Department of Chemistry Zhejiang University Hangzhou 310027 P. R. China.
Jun
J
Wu
3-methylbenzofurans; beta-glucuronidase activity; chemical elicitors; diversity-oriented synthesis; insect pests