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.
Similar content being viewed by others
References
K. R. Kuang and A. M. Lu, Flora of China, Vol. 67, Beijing Science and Technology Press, Beijing, China, 2005, p. 248.
A. Rodgman and T. A. Perfetti, The Chemical Components of Tobacco and Tobacco Smoke, CRC Press, Taylor and Francis Group, Boca Raton, Florida, 2008.
A. Fuchs, W. Slobbe, P. C. Mol, and M. A. Posthumus, Phytochemistry, 22, 1197 (1983).
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).
X. Feng, Xin, J. S. Wang, J. Luo, and L. Y. Kong, J. Asian Nat. Prod. Res., 12, 252 (2010).
G. Y. Yang, W. Zhao, Y. K. Chen, Z. Y. Chen, Q. F. Hu, and M. M. Miao, Asian J. Chem., 25, 4932 (2013).
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).
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).
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).
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).
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).
Z. Y. Chen, J. L. Tan, G. Y. Yang, M. M. Miao, Z. Y. Chen, and T. F. Li, Phytochem. Lett., 5, 233 (2012).
Y. K. Li, Y. L. Zhao, N. J. Xiang, L. Yang, F. Wang, G. Y. Yang, and Z. Y. Wang, Heterocycles, 89, 2771 (2014).
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).
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).
J. L. Tan, Z. Y. Chen, G. Y. Yang, M. M. Miao, Y. K. Chen, and T. F. Li, Heterocycles, 83, 2381 (2011).
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).
G. Y. Yang, W. Zhao, T. Zhang, Y. X. Duan, Z. H. Liu, M. M. Miao, and Y. K. Chen, Heterocycles, 89, 183 (2014).
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).
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).
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).
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).
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).
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).
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).
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).
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).
Author information
Authors and Affiliations
Corresponding authors
Additional information
Published in Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2017, pp. 751–753.
Rights and permissions
About this article
Cite this article
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
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-017-2147-4