Two new coumarins, 6-hydroxy-7-methyl-3-(4′-methoxyphenyl)-coumarin (1) and 6-hydroxy-5-methoxy-7-methyl-3-(4′-methoxyphenyl)-coumarin (2), together with five known coumarins (3–7), were isolated from the leaves of Nicotiana tabacum. Their structures were determined by means of HR-ESI-MS and extensive 1D and 2D NMR spectroscopic studies. Compounds 1–7 were tested for their anti-tobacco mosaic virus (anti-TMV) activities. Compound 2 showed high anti-TMV activity with inhibition rate of 28.6%. This rate is close to that of the positive control. The other compounds also showed potential anti-TMV activity with inhibition rates in the ranges of 13.7–23.2%, respectively.
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The Editorial Committee of the Administration Bureau of Flora of China, Flora of China, Vol. 67, Beijing Science and Technology Press, Beijing, 2005.
A. Rodgman and T. A. Perfetti, The Chemical Components of Tobacco and Tobacco Smoke. CRC Press, Taylor and Francis, Boca Raton, Florida, 2008.
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).
G. Y. Yang, W. Zhao, Y. K. Chen, Z. Y. Chen, Q. F. Hu, and M. M. Miao, Asian. J. Chem., 25, 4932 (2013).
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).
T. Braumann, G. Nicolaus, W. Hahn, and H. Elmenhorst, Phytochemistry, 29, 3693 (1990).
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).
J. X. Chen, H. Q. Leng, Y. X. Duan, W. Zhao, G. Y. Yang, Y. D. Guo, Y. K. Chen, and Q. F. Hu, Phytochem. Lett., 6, 144 (2013).
W. Zhao, L. Li, P. Lei, L. Yang, S. Z. Shang, J. G. Tang, G. Y. Yang, Y. K. Chen, and M. M. Miao, Phytochem. Lett., 12, 125 (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).
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, Mi. 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).
H. N. Lv, S. Wang, K. W. Zeng, J. Li, X. Y. Guo, D. Ferreira, J. K. Zjawiony, P. F. Tu, and Y. Jiang, J. Nat. Prod., 78, 279 (2015).
D. Q. Yu and J. S. Yang, Handbook of Analytical Chemistry (7th Volume), Nuclear Magnetic Resonance Spectroscopy, Chemical Industry Press, 2nd Ed., Beijing, 1999.
A. Hitoshti, K. Ichiro, I. Kazuhiko, and I. Kazuo, J. Nat. Prod., 49, 366 (1986).
J. H. Lee, H. B. Bang, S. Y. Han, and J. G. Jun, Tetrahedron Lett., 48, 2889 (2007).
C. Lei, W. X. Xu, J. Wu, S. J. Wang, J. Q. Sun, Z. Y. Chen, and G. Y. Yang, Chem. Nat. Compd., 51, 43 (2015).
Y. K. Li, B. Zhou, X. X. Wu, G. Du, Y. Q. Ye, X. M. Gao, and Q. F. Hu, Chem. Nat. Compd., 51, 50 (2015).
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).
Acknowledgment
This research was supported by the National Natural Science Foundation of China (No. 31360081), the Basic Research Foundation of Yunnan Province (2013FB097), and the Basic Research Foundation of Yunnan Tobacco Industry Co. Ltd (2012JC01).
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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2016, pp. 852–854.
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Liu, CB., Shen, QP., Wang, Y. et al. Coumarins from the Leaves of Nicotiana tabacum and Their Anti-Tobacco Mosaic Virus Activities. Chem Nat Compd 52, 992–995 (2016). https://doi.org/10.1007/s10600-016-1844-8
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DOI: https://doi.org/10.1007/s10600-016-1844-8