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Two New Antibacterial Naphthoquinones from a Cigar Tobacco-Derived Endophytic Fusarium solani

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In this study, two new (1 and 2), together with five known (3–7) naphthoquinones were isolated from the cigar tobacco-derived endophytic Fusarium solani. Their structures were determined by means of HR-ESI-MS and extensive 1D and 2D NMR spectroscopic studies. The new compounds were evaluated for antibacterial activities against Pseudomonas syringae (the main pathogenic sources of tobacco angular leaf spot disease). Interestingly, compounds 1 and 2 exhibited inhibitory effects with MIC50 values of 6.8 and 5.9 μg/mL, respectively. These rates are lower than that of the positive control (agricultural streptomycin, with MIC50 of 2.2 μg/mL).

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References

  1. J. L. Azevedo, W. J. Maccheroni, J. O. Pereira, and W. L. de Araujo, Electron. J. Biotechnol., 3, 15 (2000).

    Article  Google Scholar 

  2. R. Toghueo, D. Sahal, and F. F. Boyom, Phytochemistry, 174, 112338 (2020).

    Article  CAS  PubMed  Google Scholar 

  3. R. H. Zheng, S. J. Li, X. Zhang, and C. Q. Zhao, Int. J. Mol. Sci., 22, 959 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. M. Bradaric, J. Nat. Prod., 84 (6), 1860 (2021).

    Article  CAS  Google Scholar 

  5. A. G. Duran, N. Chinchilla, J. Molinillo, and F. A. Macias, Pest. Manag. Sci., 75 (9), 2517 (2019).

    Article  CAS  PubMed  Google Scholar 

  6. A. V. Pinto and S. Castro, Molecules, 14 (11), 4570 (2009).

    Article  PubMed  Google Scholar 

  7. H. Y. Qiu, P. F. Wang, H. Y. Lin, C. Y. Tang, H. L. Zhu, and Y. H. Yang, Chem. Biol. Drug. Des., 91 (3), 681 (2018).

    Article  CAS  PubMed  Google Scholar 

  8. N. Chinchilla, G. A. Guerrero-Vasquez, R. M. V. Arela, J. M. G. Molinillo, and F. A. Macias, Res. Chem. Intermed., 43, 4387 (2017).

    Article  CAS  Google Scholar 

  9. A. G. Medentsev and V. K. Akimenko, Phytochemistry, 31 (1), 77 (1992).

    Article  CAS  Google Scholar 

  10. M. G. Kim and H. S. Lee, Appl. Biol. Chem., 59, 3 (2016).

    Article  CAS  Google Scholar 

  11. R. Pavela, Ind. Crop. Prod., 43, 745 (2013).

    Article  CAS  Google Scholar 

  12. X. F. Shang, Y. Q. Liu, X. Guo, X. L. Miao, C. Chen, J. X. Zhang, X. S. Xu, G. Z. Yang, C. J. Yang, J. C. Li, and X. S. Zhang, Sci. Rep., 8, 1609 (2018).

    Article  PubMed  PubMed Central  Google Scholar 

  13. C. Silva, O. A. Chaves, R. Paiva, G. Costa, J. C. Netto-Ferreira, and A. Echevarria, J. Braz. Chem. Soc., 31 (9), 1838 (2020).

    Google Scholar 

  14. Y. Luo, H. Y. Shen, Q. X. Shen, Z. H. Cao, M Zhang, S. Y. Long, Z. B. Wang, and J. W. Tan, J. Asian. Nat. Prod. Res., 19 (9), 869 (2017).

    Article  CAS  PubMed  Google Scholar 

  15. M. D. Vukic, N. L. Vukovic, G. T. Djelic, S. L. Popovic, M. M. Zaric, D. D. Baskic, G. B. Krstic, V. V. Tesevic, and M. M. Kacaniova, Excli. J., 16, 73 (2017). https://doi.org/10.17179/excli2016-762.

  16. J. M. Sanchez-Calvo, G. R. Barbero, G. Guerrero-Vasquez, A. G. Duran, M. Macias, M. A. Rodriguez-Iglesias, J. M. G. Molinillo, and F. A. Macias, Med. Chem. Res., 25, 1274 (2016).

    Article  CAS  Google Scholar 

  17. L. P. Borba-Santos, C. D. Nicoletti, T. Vila, P. G. Ferreira, C. F. Araujo-Lima, B. V. Dias Galvao, I. Felzenszwalb, W. de Souza, F. de Carvalho da Silva, Vi. F. Ferreira, D. O. Futuro, and S. Rozental, Braz. J. Microbiol., 53, 749 (2022).

  18. M. X. Guo, J. Liu, Z. L. Xu, J. Wang, T, T. Li, H. T. Lei, X. W. Duan, Y. M. Sun, X. Y. Zhang, and R. M. Huang, J. Agric. Food Chem., 68 (36), 9697 (2020).

  19. I. Imazaki and I. Kadota, FEMS. Microbiol. Ecol., 91 (9), fiv098 (2015).

  20. R. M. T. Kouipou, Mycology, 11 (1), 1 (2020).

    Article  Google Scholar 

  21. R. Y. Guo, X. Cai, Q. Li, Y. Huang, B. K. Chen, P. Guan, J. T. Tang, and X. W. Zou, Biomed. Chromatogr., 33 (3), e4574 (2019).

    Article  PubMed  Google Scholar 

  22. J. Jeleni, J. Osi, M. Velki, and J. Ili, Fungal. Ecol., 54, 101114 (2021).

    Article  Google Scholar 

  23. A. B. Robert, H. T. James, and N. Stanley, J. Physiol. Biochem., 71, 951 (1981).

    Google Scholar 

  24. X. Y. Pang, Xi. P. Lin, Y. Q. Tian, R. Liang, J. F. Wang, B. Yang, X. F. Zhou, K. Kaliyaperumal, X. Y. Luo, Z. C. Tu, and Y. H. Liu, Nat. Prod. Res., 32 (1), 105 (2018).

  25. T. D. Zerihun, S. Beauty, G. Marieka, and V. R. Teunis, Nat. Prod. Res., 30, 1301 (2016).

    Article  Google Scholar 

  26. N. S. Chowdhury, M. H. Sohrab, M. S. Rana, C. M. Hasan, S. Jamshidi, and K. M. Rahman, J. Nat. Prod., 80, 1173 (2017).

    Article  CAS  PubMed  Google Scholar 

  27. G. Y. Yang, J. M. Dai, Q. L. Mi, Z. J. Li, Xue-Mei Li, J. D. Zhang, J. Wang, Y. K. Li, W. G. Wang, M. Zhou, and Q. F. Hu, Phytochemistry, 198, 113137 (2022).

  28. G. Diana, Diseases of Tobacco: Bacteria, Informatore Fitopatologico, 1994, pp. 29–32.

  29. C. G. Pierce, P. Uppuluri, A. R. Tristan, F. L. Wormley Jr. E. Mowat, G. Ramage, and J. L. Lopez-Ribot, Nat. Protoc., 3, 1494 (2008).

  30. L. P. Chi, X. M. Li, Y. P. Wan, Y. H. Li, X. Li, and B. G. Wang, Chem. Biodiv., 18, e2100512 (2021).

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This project was supported by the Foundation of the China Tobacco Monopoly Bureau Grants and Yunnan Provincial Tobacco Monopoly Bureau Grants (110202103018, 2022530000241004), the National Natural Science Foundation of China (No. 32260111), and the Foundation of Yunnan Innovative Research Team (2019HC020).

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Correspondence to Qiu-Fen Hu or Gao-Kun Zhao.

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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2023, pp. 889–892.

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Qiu, WY., Chen, MS., Wu, YP. et al. Two New Antibacterial Naphthoquinones from a Cigar Tobacco-Derived Endophytic Fusarium solani. Chem Nat Compd 59, 1051–1055 (2023). https://doi.org/10.1007/s10600-023-04194-2

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  • DOI: https://doi.org/10.1007/s10600-023-04194-2

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