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
Dec 8, 2005·Annual Review of Entomology·Murray B Isman
May 6, 2009·Angewandte Chemie·Sylvia KirchbergArmido Studer
Apr 27, 2012·Biochimie·Ji Hong HwangDong Gun Lee
May 9, 2013·World Journal of Microbiology & Biotechnology·Sawai BoukaewPoonsuk Prasertsan
Jan 28, 2014·Journal of Agricultural and Food Chemistry·Hongjian SongQingmin Wang
Apr 23, 2014·Organic & Biomolecular Chemistry·Hai-Xia JiangBiao Jiang
Sep 12, 2014·Angewandte Chemie·Terry TomakinianGuillaume Vincent
Aug 11, 2015·Journal of Medicinal Chemistry·Shailesh N MistryJ Robert Lane
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
Feb 1, 2018·Pest Management Science·Zhi-Jun ZhangGuo-Hua Zhong
Jun 24, 2018·Pesticide Biochemistry and Physiology·Yaqin XiangXiaolan Liao
Aug 24, 2018·Journal of Agricultural and Food Chemistry·Zhi-Jun ZhangGuo-Hua Zhong
Dec 19, 2018·International Journal of Molecular Sciences·Junmin XiGuohua Zhong
Nov 1, 2005·Plant Disease·D E Groth
May 1, 2004·Plant Disease·Twng Wah MewPham Van Du