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Evolution from Natural β-Carboline Alkaloids to Obtain 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene Derivatives as Potent Fungicidal Agents against Rhizoctonia solani

Key Laboratory of Crop Integrated Pest Management in South China, Ministry of Agriculture, South China Agricultural University, Guangzhou 510642, China
*
Author to whom correspondence should be addressed.
These authors contributed equally to this work.
Int. J. Mol. Sci. 2018, 19(12), 4044; https://doi.org/10.3390/ijms19124044
Received: 5 November 2018 / Revised: 5 December 2018 / Accepted: 10 December 2018 / Published: 14 December 2018
(This article belongs to the Section Molecular Plant Sciences)
Rice sheath blight, caused by Rhizoctonia solani, is a globally important rice disease and the increasing resistance of this pathogen highlights the need for new active compounds against rice sheath blight. In this study, natural β-carboline alkaloids were optimized to obtain a series of 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene derivatives and evaluated for their fungicidal activity and mode of action against R. solani. Of these compounds, 18 exhibited significant in vitro fungicidal activity against R. solani, with an EC50 value of 2.35 μg/mL, and was more active than validamycin A. In vivo bioassay also demonstrated that 18 displayed superior protective and curative activities as compared to validamycin A. Mechanistically, 18 not only induced the loss of mitochondrial membrane potential and accumulation of reactive oxygen species, but also interfered with DNA synthesis. Therefore, compound 18 displayed pronounced in vitro and in vivo fungicidal activity against R. solani and could be used as a potential candidate for the control of rice sheath blight. View Full-Text
Keywords: β-carboline; 1,2,4,9-tetrahydro-3-thia-9-azafluorene; fungicidal activity; Rhizoctonia solani β-carboline; 1,2,4,9-tetrahydro-3-thia-9-azafluorene; fungicidal activity; Rhizoctonia solani
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MDPI and ACS Style

Xi, J.; Zhang, Z.; Zhu, Q.; Zhong, G. Evolution from Natural β-Carboline Alkaloids to Obtain 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene Derivatives as Potent Fungicidal Agents against Rhizoctonia solani. Int. J. Mol. Sci. 2018, 19, 4044. https://doi.org/10.3390/ijms19124044

AMA Style

Xi J, Zhang Z, Zhu Q, Zhong G. Evolution from Natural β-Carboline Alkaloids to Obtain 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene Derivatives as Potent Fungicidal Agents against Rhizoctonia solani. International Journal of Molecular Sciences. 2018; 19(12):4044. https://doi.org/10.3390/ijms19124044

Chicago/Turabian Style

Xi, Junmin, Zhijun Zhang, Qi Zhu, and Guohua Zhong. 2018. "Evolution from Natural β-Carboline Alkaloids to Obtain 1,2,4,9-tetrahydro-3-thia-9-aza-fluorene Derivatives as Potent Fungicidal Agents against Rhizoctonia solani" International Journal of Molecular Sciences 19, no. 12: 4044. https://doi.org/10.3390/ijms19124044

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