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Antiviral Isoquinolines from the Cigar Tobacco Derived Endophytic Fungi Aspergillus fumigatus

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Chemistry of Natural Compounds Aims and scope

With the aim of screening more antiviral activity metabolites, in this study, two new (1 and 2), together with five known (3–7), isoquinolines were isolated from the cigar tobacco-derived endophytic fungi Aspergillus fumigatus. Their structures were determined by means of HR-ESI-MS and extensive 1D and 2D NMR spectroscopic studies. Interestingly, the anti-TMV activities test revealed that compounds 1 and 2 showed potential anti-TMV activities with inhibition rates of 31.2 and 28.5%, respectively.

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References

  1. A. Elnahal, M. T. El-Saadony, A. M. Saad, E. M. Desoky, A. M. El-Ta han, M. M. Rady, S. F. Abu Qamar, and K. A. El-Tarabily, Eur. J. Plant. Pathol., 162 (4), 759 (2022).

  2. K. H. Chen and N. Jessica, J. Exp. Bot., 73 (13), 4496 (2022).

    Article  CAS  PubMed  Google Scholar 

  3. L. O. Omoarelojie and J. V. Staden, S. Afr. J. Bot., 134, 280 (2020).

    CAS  Google Scholar 

  4. A. Hagag, M. F. Abdelwahab, A. El-Kader, and M. A. Fouad, J. Appl. Microbiol., 132 (6), 4150 (2022).

    Article  PubMed  Google Scholar 

  5. K. L. Yang, J. Tian, and N. P. Keller, Environ. Microbiol., 24 (7), 2857 (2022).

    Article  PubMed  PubMed Central  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  7. J. M. Dai, Q. L. Mi. X. M. Li, D. Gang, G. Y. Yang, J. D. Zhang, J. Wang, Y. K. Li, H. Y. Yang, M. Dong, Z. J. Li, and Q. F. Hu, Phytochemistry, 205, 113485 (2023).

  8. Y. N. Zhu, M. X. Liu, B. B. Cai, Y. Li, M. F. Li, H. S. Wang, M. Zhou, G. Y. Yang, Q. F. Hu, and Y. K. Li, Chem. Nat. Compd., 58, 712 (2022).

    Article  CAS  Google Scholar 

  9. M. F. Li, D. Xiao, L. C. Zhu, L. Liu, J. N. Zheng, X. J. Gu, Y. N. Zhu, J. Xie, X. Wang, J. M. Dai, Q. L. Mi, Y. K. Yang, Q. F. Hu, Y. K. Li, and J. Q. Shi, Chem. Nat. Compd., 58, 1093 (2022).

    Article  CAS  Google Scholar 

  10. W. G. Wang, L. Q. Du, S. L. Sheng, A. Li, Y. P. Li, G. G. Cheng, G. P. Li, G. L. Sun, Q. F. Hu, and Y. Matsuda, Org. Chem. Front., 6, 571 (2019).

    Article  CAS  Google Scholar 

  11. L. Yuan, W. Z. Huang, K. Zhou, Y. D. Wang, W. Dong, G. Du, X. M. Gao, Y. H. Ma, and Q. F. Hu, Nat. Prod. Res., 29, 1914 (2015).

    Article  CAS  PubMed  Google Scholar 

  12. M. Zhou, G. Du, H. Y. Yang, C. F. Xia, J. X. Yang, Y. Q. Ye, X. M. Gao, X. N. Li, and Q. F. Hu, Planta Med., 81, 235 (2015).

    Article  CAS  PubMed  Google Scholar 

  13. M. Zhou, K. Zhou, P. He, K. M. Wang, R. Z. Zhu, Y. D. Wang, W. Dong, G. P. Li, H. Y. Yang, Y. Q. Ye, G. Du, X. M. Li, and Q. F. Hu, Planta Med., 82, 414 (2016).

    Article  CAS  PubMed  Google Scholar 

  14. M. Zhou, J. Lou, Y. K. Li, Y. D. Wang, K. Zhou, B. K. Ji, W. Dong, X. M. Gao, G. Du, and Q. F. Hu, Arch. Pharm. Res., 40, 32 (2017).

    Article  CAS  PubMed  Google Scholar 

  15. J. M. Dai, L. C. Zhu, D. Xiao, J. Xie, X. Wang, Q. L. Mi, J. Q. Shi, G. Y. Yin, Y. K. Yang, G. Y. Yang, Q. F. Hu, and W. Kai, Chem. Nat. Compd., 58, 1005 (2022).

    Google Scholar 

  16. B. Debnath, W. S. Singh, M. Das, S. Goswami, M. K. Singh, D. Maiti, and K. Manna, Mater. Today Chem., 9, 56 (2018).

    Article  CAS  Google Scholar 

  17. M. Mohammad-Taghi, K. Ali Karimi, and L. Zahra, Toxin. Rev., 37 (1), 11 (2018).

  18. Q. Li, C. M. Chen, Y. He, M. S. Wei, L. Cheng, X. Kang, J. P. Wang, X. C. Hao, H. C. Zhu, and Y. H Zhang, Phytochemistry, 169, 112177 (2020).

    Article  CAS  PubMed  Google Scholar 

  19. 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 

  20. C. M. Liu, F. H. Yao, X. H. Lu, X. X. Zhang, L. X. Luo, X. Liang, and S. H. Qi, Mar. Drugs., 20, 78 (2022).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  21. Y. G. Sun, H. B. Liu, H. J. Gao, B. S. Lin, X. H. Xiang, H. K. Lu, Y. H. Wu, and X. H. Ma, Chin. Tob. Sci., 40 (3), 91 (2019).

    Google Scholar 

  22. C. Nord, J. J. Levenfors, J. Bjerketorp, C. Sahlberg, B. Guss, B. Ober, and A. Broberg, Molecules, 24, 4616 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. J. Kohno, H. Hiramatsu, M. Nishio, M. Sakurai, T. Okuda, and S. Komatsubara, Tetrahedron, 55 (37), 11247 (1999).

    Article  CAS  Google Scholar 

  24. F. Zhu, G. Y. Chen, J. S. Wu, and J. H. Pan, Nat. Prod. Res., 27 (21), 1960 (2013).

    Article  CAS  PubMed  Google Scholar 

  25. M. El-Aasr, D. Eliwa, M. Albadry, A. S. Ibrahim, A. Kabbash, K. M. Meepagala, I. A. Khan, S. I. Khan, and S. A. Ross, Phytochemistry, 189, 112828 (2021).

    Article  CAS  PubMed  Google Scholar 

  26. D. N. Quang, J. Schmidt, A. Porzel, L. Wessjohann, M. Haid, and N. Arnold, Nat. Prod. Commun., 5 (6), 869 (2010).

    CAS  PubMed  Google Scholar 

  27. Q. F. Hu, L. M. Liao, H. T. Huang, Y. Xu, J. Wang, W. S. Kong, Q. L. Mi, M. Zhou, G. Y. Yang, and C. M. Song, Chem. Nat. Compd., 56, 500 (2020).

    Article  CAS  Google Scholar 

  28. D. Luo, N. Lv, L. J. Zhu, L. M. Liao, Y. Xu, J. Wang, W. S. Kong, H. T. Huang, M. Zhou, G. Y. Yang, Q. F. Hu, and X. X. Si, Chem. Nat. Compd., 56, 504 (2020).

    Article  CAS  Google Scholar 

  29. Z. X. Qing, P. Yang, Q. Tang, P. Cheng, X. B. Liu, Y. J. Zheng, Y. S. Liu, and J. G. Zeng, Curr. Org. Chem., 21 (18), 1920 (2017).

    Article  CAS  Google Scholar 

  30. G. Y. Yang, J. M. Dai, Z. J. Li, J. Wang, F. X. Yang, X. Liu, J. Li, Q. Gao, X. M. Li, Y. K. Li, W. G. Wang, M. Zhou, and Q. F. Hu, Arch. Pharm. Res., 45, 572 (2022).

    Article  CAS  PubMed  Google Scholar 

  31. Q. F. Hu, Y. Y. Ma, H. Y. Liu, J. M. Dai, F. X. Yang, J. D. Zhang, J. Wang, X. M. Li, X. Liu, J. Li, Y. K. Li, W. G. Wang, M. Zhou, and G. Y. Yang, Chem. Biol. Technol. Agric., 9, 88 (2022).

    Article  CAS  Google Scholar 

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Acknowledgment

This project was supported by the Foundation of the China Tobacco Monopoly Bureau Grants and Yunnan Provincial Tobacco Monopoly Bureau Grants (110202103018, 2022530000241002), the National Natural Science Foundation of China (No. 32260111), and the Foundation of Yunnan Innovative Research Team (2019HC020).

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Authors and Affiliations

  1. Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicina Endophytes, Yunnan Minzu University, 650500, Kunming, P. R. China

    Gui Pu, Xue-Ju Cha, Yue-Yu Ma & Qiu-Fen Hu

  2. Yunnan Academy of Tobacco Agricultural Sciences, 650021, Kunming, P. R. China

    Gui Pu, Rui-Feng Xiong, Guang-Hai Zhang, Heng Yao, Yu-Ping Wu, Yin-Ke Li & Guang-Hui Kong

  3. Kunming Institute of Botany, Chinese Academy of Sciences, 650201, Kunming, P. R. China

    Mei-Fen Bao

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  1. Gui Pu
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Correspondence to Qiu-Fen Hu or Guang-Hui Kong.

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Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2023, pp. 739–742.

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Pu, G., Cha, XJ., Ma, YY. et al. Antiviral Isoquinolines from the Cigar Tobacco Derived Endophytic Fungi Aspergillus fumigatus. Chem Nat Compd 59, 876–880 (2023). https://doi.org/10.1007/s10600-023-04139-9

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  • DOI: https://doi.org/10.1007/s10600-023-04139-9

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