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Two New 2-Arylbenzofurans from the Stems of Nicotiana tabacum and Their Bioactivities

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Chemistry of Natural Compounds Aims and scope

Two new 2-arylbenzofurans, 2-(4-methoxyphenyl)-3,5-dimethylbenzofuran-7-ol (1) and 2-(4-methoxyphenyl)-3,5-dimethylbenzofuran-6-ol (2), were isolated from the stems of Nicotiana tabacum. Their structures were determined by means of HR-ESI-MS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1 and 2 were tested for their anti-TMV and cytotoxicity activities. The results showed that compounds 1 and 2 exhibited high anti-TMV activities with inhibition rates of 29.2% and 30.8% at the concentration of 20 μM. These rates are close to that of positive control (31.1%). Compounds 1 and 2 also showed moderate to weak cytotoxicities against the tested human tumor cell lines with IC50 values in the range of 2.2–8.2 μM.

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References

  1. K. R. Kuang and A. M. Lu, Flora of China, Vol. 67, Beijing Science and Technology Press, Beijing, China, 2005, p. 248.

  2. A. Rodgman and T. A. Perfetti, The Chemical Components of Tobacco and Tobacco Smoke, CRC Press, Taylor and Francis Group, Boca Raton, Florida, 2008.

    Google Scholar 

  3. A. Fuchs, W. Slobbe, P. C. Mol, and M. A. Posthumus, Phytochemistry, 22, 1197 (1983).

    Article  CAS  Google Scholar 

  4. 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 

  5. X. Feng, Xin, J. S. Wang, J. Luo, and L. Y. Kong, J. Asian Nat. Prod. Res., 12, 252 (2010).

  6. G. Y. Yang, W. Zhao, Y. K. Chen, Z. Y. Chen, Q. F. Hu, and M. M. Miao, Asian J. Chem., 25, 4932 (2013).

    CAS  Google Scholar 

  7. G. H. Kong, Y. P. Wu, W. Li, Z. Y. Xia, Q. Liu, K. M. Wang, P. He, R. Z. Zhu, X. X. Si, and G. Y. Yang, Heterocycles, 92, 331 (2016).

    Article  CAS  Google Scholar 

  8. X. C. Wei, S. C. Sumithran, A. G. Deaciuc, H. R. Burton, L. P. Bush, L. P. Dwoskin, and P. A. Crooks, Life Sci., 78, 495 (2005).

    Article  CAS  PubMed  Google Scholar 

  9. Y. K. Chen, X. S. Li, G. Y. Yang, Z. Y. Chen, Q. F. Hu, and M. M. Miao, J. Asian Nat. Prod. Res., 14, 450 (2012).

    Article  CAS  PubMed  Google Scholar 

  10. X. M. Gao, X. S. Li, X. Z. Yang, H. X. Mu, Y. K. Chen, G. Y. Yang, and Q. F. Hu, Heterocycles, 85, 147 (2012).

    Article  CAS  Google Scholar 

  11. M. M. Miao, L. Li, Q. P. Shen, C. B. Liu, Y. K. Li, T. Zhang, F. M. Zhang, P. He, K. M. Wang, R. Z. Zhu, Y. K. Chen, and G. Y. Yang, Fitoterapia, 103, 260 (2015).

    Article  CAS  PubMed  Google Scholar 

  12. Z. Y. Chen, J. L. Tan, G. Y. Yang, M. M. Miao, Z. Y. Chen, and T. F. Li, Phytochem. Lett., 5, 233 (2012).

    Article  CAS  Google Scholar 

  13. Y. K. Li, Y. L. Zhao, N. J. Xiang, L. Yang, F. Wang, G. Y. Yang, and Z. Y. Wang, Heterocycles, 89, 2771 (2014).

    Article  CAS  Google Scholar 

  14. Y. Wang, C. B. Liu, Q. P. Shen, F. M. Zhang, P. He, Z. H. Liu, H. B. Zhang, X. D. Yang, M. M. Miao, and G. Y. Yang, Heterocycles, 91, 1198 (2015).

    Article  CAS  Google Scholar 

  15. H. Q. Leng, J. X. Chen, Y. Hang, Y. X. Duan, G. Y. Yang, Y. K. Chen, Y. D. Guo, Q. F. Hu, and M. M. Miao, Chem. Nat. Compd., 49, 1028 (2014).

    Article  CAS  Google Scholar 

  16. J. L. Tan, Z. Y. Chen, G. Y. Yang, M. M. Miao, Y. K. Chen, and T. F. Li, Heterocycles, 83, 2381 (2011).

    Article  CAS  Google Scholar 

  17. D. R. Mou, W. Zhao, T. Zhang, L. Wan, G. Y. Yang, Y. K. Chen, Q. F. Hu, and M. M. Miao, Heterocycles, 85, 2485 (2012).

    Article  CAS  Google Scholar 

  18. G. Y. Yang, W. Zhao, T. Zhang, Y. X. Duan, Z. H. Liu, M. M. Miao, and Y. K. Chen, Heterocycles, 89, 183 (2014).

    Article  CAS  Google Scholar 

  19. S. Z. Shang, W. X. Xu, P. Lei, W. Zhao, J. G. Tang, M. M. Miao, H. D. Sun, J. X. Pu, Y. K. Chen, and G. Y. Yang, Fitoterapia, 99, 35 (2014).

    Article  CAS  PubMed  Google Scholar 

  20. S. Z. Shang, Y. X. Duan, X. Zhang, J. X. Pu, H. D. Sun, Z. Y. Chen, M. M. Miao, G. Y. Yang, and Y. K. Chen, Phytochem. Lett., 7, 413 (2014).

    Google Scholar 

  21. S. Z. Shang, W. X. Xu, L. Li, J. G. Tang, W. Zhao, P. Lei, M. M. Miao, H. D. Sun, J. X. Pu, Y. K. Chen, and G. Y. Yang, Phytochem. Lett., 11, 53 (2015).

    Article  CAS  Google Scholar 

  22. Q. Wang, S. Ji, S. W. Yu, H. X. Wang, X. H. Lin, T. T. Ma, X. Qiao, C. Xiang, M. Ye, and D. A. Guo, Fitoterapia, 85, 35 (2013).

    Article  CAS  PubMed  Google Scholar 

  23. M. Zhou, K. Zhou, X. M. Gao, Z. Y. Jiang, J. J. Lv, Z. H. Liu, G. Y. Yang, M. M. Miao, C. T. Che, and Q. F. Hu, Org. Lett., 17, 2638 (2015).

    Article  CAS  PubMed  Google Scholar 

  24. 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 

  25. Q. F. Hu, B. Zhou, J. M. Huang, Z. Y. Jiang, X. Z. Huang, L. Y. Yang, X. M. Gao, G. Y. Yang, and C. T. Che, J. Nat. Prod., 76, 1866 (2013).

    Article  CAS  PubMed  Google Scholar 

  26. Q. F. Hu, B. Zhou, Y. Q. Ye, Z. Y. Jiang, X. Z. Huang, Y. K. Li, G. Du, G. Y. Yang, and X. M. Gao, J. Nat. Prod., 76, 1854 (2013).

    Article  CAS  PubMed  Google Scholar 

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Acknowledgment

This research was supported by the National Natural Science Foundation of China (Nos. 21562049, 31360081, and 31400303), the Applied Fundamental Foundation of Yunnan Province (Nos. 2014FB163, 2015FB162), and the Research Foundation of China Tobacco Company (No. 110201502006).

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Correspondence to Xue-Mei Li or Yadong Guo.

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Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2017, pp. 751–753.

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Xu, X., Shi, J., Li, C. et al. Two New 2-Arylbenzofurans from the Stems of Nicotiana tabacum and Their Bioactivities. Chem Nat Compd 53, 883–886 (2017). https://doi.org/10.1007/s10600-017-2147-4

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  • DOI: https://doi.org/10.1007/s10600-017-2147-4

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