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Chromones from the Tobacco Derived Fungus Aspergillus versicolor and Their Antiviral Activity

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Chemistry of Natural Compounds Aims and scope

Two new chromones, 8-(3-hydroxypropyl)-2-(3-hydroxy-1-oxopropyl)-6-methoxy-4H-chromen-4-one (1), 2-acetyl-8-(3-hydroxypropyl)-6-methoxy-4H-chromen-4-one (2), along with four known ones (3–6) were isolated from the fermentation products of an endophytic fungus Aspergillus versicolor derived from tobacco. Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were evaluated for their anti-tobacco mosaic virus (anti-TMV) activities. The results showed that compounds 1 and 2 exhibited potential anti-TMV activities with inhibition rates of 35.3 and 30.6%, respectively, rates that are close to that of positive control.

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References

  1. R. S. Keri, S. Budagumpi, R. K. Pai, and R. G. Balakrishna, Eur. J. Med. Chem., 78, 340 (2014).

    Article  CAS  PubMed  Google Scholar 

  2. R. B. Semwal, D. K. Semwal, S. Combrinck, and A. Viljoen, Phytochem. Rev., 19, 761 (2020).

    Article  CAS  Google Scholar 

  3. N. A. Mohsin, M. Irfan, S. Hassan, and U. Saleem, Pharm. Chem. J., 54, 241 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  4. S. Techaoei, C. Jirayuthcharoenkul, K. J. Kom, T. Dumrongphuttidecha, and W. Khobjai, Saudi J. Biol. Sci., 27, 2883 (2020).

    CAS  Google Scholar 

  5. M. C. Manganyi and C. N. Ateba, Microorganisms, 8, 1934 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. S. Skanda and B. S. Vijayakumar, Curr. Microbiol., 78, 1317 (2021).

    Article  CAS  PubMed  Google Scholar 

  7. M. Y. Deng, X. Chen, Z. Y. Shi, and S. S. Xie, Fitoterapia, 151, 104882 (2021).

    Article  CAS  PubMed  Google Scholar 

  8. 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 

  9. M. Zhou, M. M. Miao, G. Du, X. N. Li, S. Z. Shang, W. Zhao, Z. H. Liu, G. Y. Yang, C. T. Che, Q. F. Hu, and X. M. Gao, Org. Lett., 16, 5016 (2014).

    Article  CAS  PubMed  Google Scholar 

  10. 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).

  11. K. Zhou, L. Zhu, X. L. Wang, T. D. Zhang, Y. D. Wang, W. Dong, B. K. Ji, H. Y. Yang, G. Du, Q. F. Hu, and M. Zhou, Chem. Nat. Compd., 52, 591 (2016).

    Article  CAS  Google Scholar 

  12. 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 

  13. 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 

  14. G. Du, Z. C. Wang, Y. K. Yang, H. M. Yang, H. Y. Yang, M. Zhou, Y. Q. Ye, X. M. Li, and Q. F. Hu, Heterocycles, 91, 1996 (2015).

    Article  CAS  Google Scholar 

  15. 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 

  16. 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 

  17. W. H. Lin, G. Brauers, R. Ebel, V. Wray, A. Berg, S. Sudarsono, and P. Proksch, J. Nat. Prod., 85, 292 (2022).

    Article  Google Scholar 

  18. Y. Liu, L. J. Ding, J. X. He, Z. M. Zhang, Y. T. Deng, S. He, and X. J. Yan, Fitoterapia, 154, 105004 (2021).

    Article  CAS  PubMed  Google Scholar 

  19. A. S. Bhagavathula, A. J. Mahmoud Al-Khatib, A. A. Elnour, N. M. S. Al Kalbani, and A. Shehabet, Pharmacogn. Res., 7, 397 (2015).

  20. D. H. Li, S. X. Cai, L. Tian, Z. J. Lin, T. J. Zhu, Y. C. Fang, P. P. Liu, Q. Q. Gu, and W. M. Zhu, Arch. Pharm. Res., 30, 1051 (2007).

    Article  CAS  PubMed  Google Scholar 

  21. Z. Abbas, B. S. Siddiqui, S. Shahzad, S. Sattar, S. Begum, A. Batool, and M. I. Choudhary, Nat. Prod. Res., 35, 4448 (2021).

    Article  CAS  PubMed  Google Scholar 

  22. F. M. Dean and M. L. Robinson, Phytochemistry, 10, 3221 (1971).

    Article  CAS  Google Scholar 

  23. P. S. Yang, J. M. Dai, X. J. Gu, W. Xiong, D. Q. Huang, S. Y. Qiu,. J. N. Zheng, Y. Li, F. X. Yang, and M. Zhou, Molecules, 27, 3129 (2022b).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. 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, https://doi.org/10.1007/s12272-022-01399-x (2022).

  25. J. R. Jiang, J. D. Zhang, G. Y. Yin, J. Q. Shi, B. B. Cai, W. W. Yang, L. L. Deng, L. Xu, T. Zhou, Q. F. Hu, M. Zhou, and W. S. Kong, Chem. Nat. Compd., 58, 414 (2022).

    Article  Google Scholar 

  26. Q. F. Hu, B. Zhou, X. M. Gao, L. Y. Yang, L. D. Shu, Y. Q. Shen, G. P. Li, C. T. Che, and G. Y. Yang, J. Nat. Prod., 75, 1909 (2012).

    Article  CAS  PubMed  Google Scholar 

  27. T. Zhou, F. X. Yang, B. B. Cai, F. Wu, Y. N. Zhu, L. Liu, C. B. Liu, J. Ling, W. S. Kong, G. Y. Yang, Q. F. Hu, and Xin Liu, Chem. Nat. Compd., 57, 1019 (2021).

    Article  CAS  Google Scholar 

  28. Q. F. Hu, B. Zhou, J. M. Huang, X. M. Gao, L. D. Shu, G. Y. Yang, and C. T. Che, J. Nat. Prod., 76, 292 (2013).

    Article  CAS  PubMed  Google Scholar 

  29. M. Zhou, M. M. Miao, G. Du, S. Z. Shang, W. Zhao, Z. H. Liu, G. Y. Yang, C. T. Che, Q. F. Hu, and X. M. Gao, Org. Lett., 16, 5016 (2014).

    Article  CAS  PubMed  Google Scholar 

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Acknowledgment

This project was supported financially by the National Natural Science Foundation of China (Nos. 81860624, 21967021), the Foundation of Yunnan Tobacco Industry Co. Ltd. (No. 2022JY02), and the Yunnan Innovative Research Team (2019HC020).

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Correspondence to Qiu-fen Hu or Xiao-Wei Ma.

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Published in Khimiya Prirodnykh Soedinenii, No. 3, May–June, 2023, pp. 392–395.

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Shen, SY., Xiong, W., Li, SS. et al. Chromones from the Tobacco Derived Fungus Aspergillus versicolor and Their Antiviral Activity. Chem Nat Compd 59, 462–466 (2023). https://doi.org/10.1007/s10600-023-04024-5

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