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

Key Laboratory of Crop Integrated Pest Management in South China, Ministry of Agriculture and Rural Affairs, South China Agricultural University, Guangzhou 510642, China

Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, South China Agricultural University, Guangzhou 510642, China

School of Pharmacy, Lanzhou University, Lanzhou 730000, China

Authors to whom correspondence should be addressed.

^†

These authors contributed equally to this work.

Academic Editor: Josphat Matasyoh

Molecules 2020, 25(5), 1189; https://doi.org/10.3390/molecules25051189

Received: 14 February 2020 / Revised: 28 February 2020 / Accepted: 2 March 2020 / Published: 6 March 2020

(This article belongs to the Section Medicinal Chemistry)

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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. View Full-Text

Keywords: β-carboline; indole; simplification; fungicidal activity; Rhizoctonia solani

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MDPI and ACS Style

Zeng, J.; Zhang, Z.; Zhu, Q.; Jiang, Z.; Zhong, G. Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight. Molecules 2020, 25, 1189. https://doi.org/10.3390/molecules25051189

AMA Style

Zeng J, Zhang Z, Zhu Q, Jiang Z, Zhong G. Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight. Molecules. 2020; 25(5):1189. https://doi.org/10.3390/molecules25051189

Chicago/Turabian Style

Zeng, Jie, Zhijun Zhang, Qi Zhu, Zhiyan Jiang, and Guohua Zhong. 2020. "Simplification of Natural β-Carboline Alkaloids to Obtain Indole Derivatives as Potent Fungicides against Rice Sheath Blight" Molecules 25, no. 5: 1189. https://doi.org/10.3390/molecules25051189

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

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