Nematicidal effect against Bursaphelenchus xylophilus of harmine quaternary ammonium derivatives, inhibitory activity and molecular docking studies on acetylcholinesterase

In the present study, we have investigated nematicidal effects against Bursaphelenchus xylophilus and inhibition potential, molecular docking of 43 harmine derivatives on acetylcholinesterase in vitro and in vivo. Among them, harmine quaternary ammonium derivatives 10 , 11 , 12 and 13 displayed prom...

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Veröffentlicht in:European journal of plant pathology 2019-01, Vol.153 (1), p.239-250
Hauptverfasser: Xia, Yan, Qi, Ya-meng, Yu, Xi-hui, Wang, Bin-feng, Cao, Ri-hui, Jiang, Ding-xin
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container_issue 1
container_start_page 239
container_title European journal of plant pathology
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creator Xia, Yan
Qi, Ya-meng
Yu, Xi-hui
Wang, Bin-feng
Cao, Ri-hui
Jiang, Ding-xin
description In the present study, we have investigated nematicidal effects against Bursaphelenchus xylophilus and inhibition potential, molecular docking of 43 harmine derivatives on acetylcholinesterase in vitro and in vivo. Among them, harmine quaternary ammonium derivatives 10 , 11 , 12 and 13 displayed promising nematicidal effects with 48 h LC 50 values of 1.63, 1.63, 1.75 and 1.44 μg/mL, respectively and remarkable inhibition effects on acetylcholinesterase (IC 50 values are 0.92, 0.90, 0.82, 0.07 μg/mL in vitro and 17.16, 14.56, 13.63, 3.06 μg/mL in vivo, respectively). The structure–activity analysis indicated that the presence of the methyl group in 1–position, the electron–donating substituents in 2–and 9–positions, bromine in 6–position, and the electron–withdrawing substituents in 7–position of carboline ring, could enhance the nematicidal effect and inhibition of acetylcholinesterase. Moreover, a molecular model was provided for the binding between compound 13 and the active site of acetylcholinesterase based on the computational docking results and helps us to optimize these new leading compounds.
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Among them, harmine quaternary ammonium derivatives 10 , 11 , 12 and 13 displayed promising nematicidal effects with 48 h LC 50 values of 1.63, 1.63, 1.75 and 1.44 μg/mL, respectively and remarkable inhibition effects on acetylcholinesterase (IC 50 values are 0.92, 0.90, 0.82, 0.07 μg/mL in vitro and 17.16, 14.56, 13.63, 3.06 μg/mL in vivo, respectively). The structure–activity analysis indicated that the presence of the methyl group in 1–position, the electron–donating substituents in 2–and 9–positions, bromine in 6–position, and the electron–withdrawing substituents in 7–position of carboline ring, could enhance the nematicidal effect and inhibition of acetylcholinesterase. 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subjects Acetylcholinesterase
Agriculture
Ammonium
Biomedical and Life Sciences
Bromine
Bursaphelenchus xylophilus
Computer applications
Derivatives
Ecology
Life Sciences
Molecular docking
Plant Pathology
Plant Sciences
title Nematicidal effect against Bursaphelenchus xylophilus of harmine quaternary ammonium derivatives, inhibitory activity and molecular docking studies on acetylcholinesterase
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