RESEARCH ARTICLE

Discovery of cryptolepine derivatives as novel promising agents against phytopathogenic bacteria

  • Ying-Hui He 1,2 ,
  • Qing-Ru Chu 2 ,
  • Shao-Yong Zhang 1 ,
  • Li-Rong Guo 2 ,
  • Yue Ma 2 ,
  • Bao-Qi Zhang 2 ,
  • Zhi-Jun Zhang 2 ,
  • Wen-Bin Zhao 2 ,
  • Yong-Mei Hu 2 ,
  • Chen-Jie Yang 2 ,
  • Sha-Sha Du 2 ,
  • Tian-Lin Wu 2 ,
  • Ying-Qian Liu , 1,2,3
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  • 1. Key Laboratory of Vector Biology and Pathogen Control of Zhejiang Province, College of Life Science, Huzhou University, Huzhou 313000, China
  • 2. School of Pharmacy, Lanzhou University, Lanzhou 730000, China
  • 3. Laboratory of Grassland Agro-ecosystems, Lanzhou University, Lanzhou 730000, China

Received date: 06 Apr 2022

Accepted date: 19 May 2022

Published date: 15 Feb 2023

Copyright

2022 Higher Education Press

Abstract

To ensure the production of food crops, a series of cryptolepine derivatives were synthesised, after which their antibacterial activities and mechanism of action against three plant pathogens were investigated. Our bioassay results indicated that most of the target compounds displayed potent inhibitory effects against Xanthomonas oryzae (X. oryzae) and Xanthomonas axonopodis pv. citri (X. axonopodis pv. c.). Remarkably, compound 9 exhibited the best in vitro antibacterial activity against X. oryzae, with a minimum inhibitory concentration (MIC) value of 0.78 μg·mL–1. Compound 2 exhibited the best in vitro antibacterial activity against X. axonopodis pv. c., with an MIC value of 0.39 μg·mL–1. These activities were superior to those of copper quinolate (MIC = 6.25, 25 μg·mL–1) and thiodiazole copper (MIC = 100, 200 μg·mL–1) against X. oryzae and X. axonopodis pv. c. In vivo experiments demonstrated the promising applicability of compound 9 for the control of rice bacterial infections. Furthermore, compound 9 was selected as a candidate to conduct preliminary analyses of the antibacterial mechanisms of cryptolepine derivatives. Scanning electron microscopy and transmission electron microscopy observations, extracellular polysaccharide production, biofilm formation, transcriptomic, quantitative reverse transcription-polymerase chain reaction analyses, and molecular docking assays were performed. Collectively, our findings demonstrated that compound 9 might act via multifarious mechanisms to down-regulate virulence factors and cause cell death.

Cite this article

Ying-Hui He , Qing-Ru Chu , Shao-Yong Zhang , Li-Rong Guo , Yue Ma , Bao-Qi Zhang , Zhi-Jun Zhang , Wen-Bin Zhao , Yong-Mei Hu , Chen-Jie Yang , Sha-Sha Du , Tian-Lin Wu , Ying-Qian Liu . Discovery of cryptolepine derivatives as novel promising agents against phytopathogenic bacteria[J]. Frontiers of Chemical Science and Engineering, 2023 , 17(2) : 156 -166 . DOI: 10.1007/s11705-022-2196-5

Acknowledgements

This work was supported financially by the National Natural Science Foundation of China (Grant Nos. 22177043 and 21877056) and the Natural Science Foundation of Gansu Province (Grant No. 20JR5RA311); the support was also supplied by the Key Program for International S&T Cooperation Projects of Gansu Province of China (Grant No. 18YF1WA115).

Electronic Supplementary Material

Supplementary material is available in the online version of this article at https://dx.doi.org/10.1007/s11705-022-2196-5 and is accessible for authorized users.
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