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Two New Benzofulvene Sesquiterpenoids from the Stems of Nicotiana tabacum and their Antibacterial Activity

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Two new benzofulvene sesquiterpenoids, tabanoids A and B (1 and 2) as well as five known sesquiterpenoids (3–7) were isolated from the stem of Nicotiana tabacum. Their structures were determined mainly by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1 and 2 were tested for their anti-methicillin-resistant Staphylococcus aureus (anti-MRSA) activity. The results revealed that compounds 1 and 2 showed good inhibition with IZD of 15.2 ± 2.5, and 12.8 ± 2.2 mm, respectively.

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References

  1. F. L. Bideau, M. Kousara, L. Chen, L. Wei, and F. Dumas, Chem. Rev., 117, 6110 (2017).

    Article  PubMed  Google Scholar 

  2. A. Maurya, S. Mohan, and S. C. Verma, Curr. Top. Med. Chem., 21 (10), 851 (2021).

    Article  CAS  PubMed  Google Scholar 

  3. B. M. Fraga, Nat. Prod. Rep., 30 (9), 1226 (2013).

    Article  CAS  PubMed  Google Scholar 

  4. J. Bezerra, F. C. Rodrigues, R. Cruz, L. Silva, and M. Braga, Appl. Sci., 10 (2), 631 (2020).

    Article  CAS  Google Scholar 

  5. A. I. Elshamy, T. A. Mohamed, E. M. Elkady, I. A. Saleh, and M. Hegazy, Antibiotics, 10, 1158 (2021).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. P. Georgantea, E. Ioannou, E. Evain-Bana, D. Bagrel, N. Martinet, C. Vagias, and V. Roussis, Tetrahedron, 47 (23), 3262 (2016).

    Article  Google Scholar 

  7. Y. H. Ding, T. P. Wang, T. Y. Chen, C. F. Xie, and Q. Zhang, Bioorg. Chem., 101, 103973 (2020).

    Article  CAS  PubMed  Google Scholar 

  8. E. Cenci, F. Messina, E. Rossi, F. Epifano, and M. C. Marcotullio, Nat. Prod. Commun., 7 (2), 143 (2012).

    CAS  PubMed  Google Scholar 

  9. M. Y. Liu, P. Li, X. L. Tang, X. C. Luo, K. C. Liu, Y. Zhang, Q. Wang, and G. Q. Li, J. Org. Chem., 86, 970 (2020).

    Article  PubMed  Google Scholar 

  10. M. Chadwick, H. Trewin, F. Gawthrop, and C. Wagstaff, Int. J. Mol. Sci., 14, 12780 (2013).

    Article  PubMed  PubMed Central  Google Scholar 

  11. B. M. Fraga, Nat. Prod. Rep., 24, 1350 (2007).

    Article  CAS  PubMed  Google Scholar 

  12. R. Vagg and S. Chapman, Addiction, 100, 701 (2015).

    Article  Google Scholar 

  13. A. R. Jassbi, S. Zare, M. Asadollahi, and M. C. Schuman, Chem. Rev., 117, 12227 (2017).

    Article  CAS  PubMed  Google Scholar 

  14. A. Rodgman and T. A. Perfetti, The Chemical Components of Tobacco and Tobacco Smoke, Second Edition, CRC Press, Taylor and Francis Group, Boca Raton, Florida, 2013.

    Google Scholar 

  15. P. S. Yang, S. Y. Tang, C. B. Liu, L. Ye, F. M. Zhang, P. He, Z. H. Liu, Y. K. Chen, M. M. Miao, Q. P. Shen, and J. Q Wang, J. Asian. Nat. Prod. Res., 21 (2), 109 (2019).

    Article  CAS  PubMed  Google Scholar 

  16. Q. P. Shen, X. M. Xu, C. B. Liu, W. Zhao, N. J. Xiang, Y. K. Chen, M. M. Miao, Z. H. Liu, and G. Y. Yang, Nat. Prod. Res., 30 (22), 2545 (2016).

    Article  CAS  PubMed  Google Scholar 

  17. S. Z. Shang, W. Zhao, J. G. Tang, X. M. Xu, H. D. Sun, J. X. Pu, Z. H. Liu, M. M. Miao, Y. K. Chen, and G. Y. Yang, Fitoterapia, 108, 1 (2016).

    Article  CAS  PubMed  Google Scholar 

  18. J. Chappell and R. Nable, Plant. Physiol., 85, 469 (1987).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. D. L. Van Tassel, O. Tesdell, B. Schlautman, M. J. Rubin, L. R. De Haan, T. E. Crews, and A. S. Krug, Front. Plant. Sci., 11, 789 (2020).

    Article  PubMed  PubMed Central  Google Scholar 

  20. A. Kessler, Curr. Opin. Insect. Sci., 8, 47 (2015).

    Article  PubMed  Google Scholar 

  21. R. Mishra, R. K. Joshi, and K. J. Zhao, Plant. Biotechnol. J., 18, 20 (2020).

    Google Scholar 

  22. T. Masuda, A. Jitoe, and N. Nakatani, Chem. Lett., 20, 1625 (1991).

    Article  Google Scholar 

  23. R. Hu, S. Z. Shang, W. Zhao, Y. K. Chen, G. Y. Yang, and Z. H. Liu, Asian J. Chem., 27, 1947 (2015).

    Article  CAS  Google Scholar 

  24. Q. P. Shen, X. M. Xu, L. Li, W. Zhao, N. J. Xiang, G. Y. Yang, Y. K. Chen, M. M. Miao, C. B. Liu, and Z. H. Liu, Chin. Chem. Lett., 27, 753 (2016).

    Article  CAS  Google Scholar 

  25. Clinical and Laboratory Standards Institute, Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically, Approved Standard, Vol. 32, Clinical and Laboratory Standards Institute, Wayne, Pa, USA, 9th edition, 2012.

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Acknowledgment

This project was supported financially by the Foundation Yunnan Tobacco Industry Co. Ltd. (No. JB2022XY03), the Foundation of Yunnan Tobacco Company (No. 2021530000241009), and the Foundation of Yunnan Innovative Research Team (2019HC020).

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Correspondence to Jie-Yun Cai.

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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2023, pp. 922–925.

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Shang, SZ., Dai, JM., Xiong, W. et al. Two New Benzofulvene Sesquiterpenoids from the Stems of Nicotiana tabacum and their Antibacterial Activity. Chem Nat Compd 59, 1092–1096 (2023). https://doi.org/10.1007/s10600-023-04203-4

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  • DOI: https://doi.org/10.1007/s10600-023-04203-4

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