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European Journal of Plant Pathology

, Volume 153, Issue 1, pp 111–122 | Cite as

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

  • Yan Xia
  • Ya-meng Qi
  • Xi-hui Yu
  • Bin-feng Wang
  • Ri-hui CaoEmail author
  • Ding-xin JiangEmail author
Article
  • 117 Downloads

Abstract

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 LC50 values of 1.63, 1.63, 1.75 and 1.44 μg/mL, respectively and remarkable inhibition effects on acetylcholinesterase (IC50 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.

Keywords

Harmine derivatives Natural product – Based nematicide Acetylcholinesterase Structure – Activity relationships Molecular docking 

Notes

Acknowledgements

The work was supported by the Science and Technology Planning Project of Guangdong Province, China [grant numbers 2016A020210082]; the Science and Technology Program of Guangzhou, China [grant numbers 201607010181]; the Science and Technology Program of Zhongshan, China [grant numbers 2016F2FC0016]; the National Natural Science Foundation of China [grant numbers 31171871]. We are grateful to Xu Zenglin (College of Food Science, South China Agricultural University) for expert assistance in molecule docking study.

Compliance with ethical standards

Conflict of interest

All authors certify that 1) they do not have any actual or potential conflict of interest, 2) the study described is original and has not been published previously, and is not under consideration for publication elsewhere, 3) all prevailing local, national and international regulations and conventions, and normal scientific ethical practices, have been respected. We also certify that all authors have reviewed the manuscript and approved the final version of manuscript before submission.

Human and animal subjects

This article does not contain any studies with human or animal subjects.

Informed consent

All the authors certify that the work carried out in this research followed the principles of ethical and professional conduct have been followed. The funders had no role in study design, data collection and analysis, decision to publish, or preparation of the manuscript.

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Copyright information

© Koninklijke Nederlandse Planteziektenkundige Vereniging 2018

Authors and Affiliations

  1. 1.Key Laboratory of Natural Pesticide and Chemical Biology, Ministry of Education, Laboratory of Insect ToxicologySouth China Agricultural UniversityGuangzhouPeople’s Republic of China
  2. 2.Zhongshan Lanju Daily Chemical Industrial Co., Ltd.ZhongshanPeople’s Republic of China
  3. 3.School of Chemistry and Chemical EngineeringSun Yat–sen UniversityGuangzhouPeople’s Republic of China

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