Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Jie ZengGuohua Zhong

Abstract

The increasing resistance of rice sheath blight caused by Rhizoctonia solani highlights the need for highly effective and environmentally benign agents. Natural β-carboline alkaloids were simplified to obtain a series of indole derivatives, and their fungicidal activity and preliminary mode of action against R. solani were also evaluated. The initial hit indole (7) displayed significant fungicidal activity with an EC50 value of 25.56 μg/mL, and was selected for further optimization. Importantly, compound 55, the most active compound, had an EC50 value of 0.62 μg/mL, and approximately 300-fold more potent than validamycin A (EC50 = 183.00 μg/mL). In vivo bioassay also demonstrated that compound 55 showed better fungicidal activities than validamycin A. Moreover, the mechanism studies revealed that compound 55 not only caused remarkable morphological and structural alterations of R. solani hyphae, but also induced the loss of mitochondrial membrane potential and interfered with DNA synthesis. Therefore, compound 55 showed superior fungicidal activity against R. solani, and the elucidated mode of action supported the potential application of compound 55 against rice sheath blight.

References

Mar 1, 2003·Journal of Pharmaceutical and Biomedical Analysis·M KartalS Kurucu
May 9, 2013·World Journal of Microbiology & Biotechnology·Sawai BoukaewPoonsuk Prasertsan
Aug 13, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zhibin LiQunfang Weng
Mar 31, 2016·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Satoshi Ichikawa
Jul 22, 2016·Current Drug Targets·Haroon KhanSurriya Amin
Feb 9, 2017·Journal of Medicinal Chemistry·Lewis D Pennington, Demetri T Moustakas
Aug 8, 2017·Mini Reviews in Medicinal Chemistry·Thokchom Prasanta Singh, Okram Mukherjee Singh
Nov 8, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zhi-Jun ZhangGuo-Hua Zhong
Aug 24, 2018·Journal of Agricultural and Food Chemistry·Zhi-Jun ZhangGuo-Hua Zhong

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Citations

Aug 28, 2021·Pesticide Biochemistry and Physiology·Feixu MoMing Li

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Methods Mentioned

BETA
acylation
column chromatography
nuclear magnetic resonance
Assay
scanning
transmission electron microscopy
fluorescence microscopy

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