Two new compounds (1 and 2), together with five known (3–7) chromone derivatives, were isolated from the stems of Nicotiana tabacum (a gene-edited mutant cultivated by Yunnan China Tobacco Industry Co., Ltd.). Their structures were elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compounds 1, 2, and 7 were tested for their anti-tobacco mosaic virus (anti-TMV) activity. The results showed that compound 1, 2, and 7 exhibited high anti-TMV activities with inhibition rates of 38.4, 43.5, and 33.6% at the concentration of 20 μM. These rates are higher than that of positive control.
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R. Shakirov, M. V. Telezhenetskaya, I. A. Bessonova, S. F. Aripova, I. A. Israilov, M. N. Sultankhodzhaev, V. I. Vinogradova, V. I. Akhmedzhanova, T. S. Tulyaganov, B. T. Salimov, and V. A. Tel′nov, Chem. Nat. Compd., 32, 596 (1996).
The Editorial Committee of the Administration Bureau of Flora of China, Flora of China, Vol. 67, Beijing Science and Technology Press, Beijing, 2005.
M. M. Goodin, D. Zaitlin, R. A. Naidu, and S. A. Lommel, Mol. Plant-Microbe Interact., 21, 1015 (2008).
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).
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).
S. K. Chien, L. C. Chen, H. C. Huang, L. C. Chen, J. W. Hsiao, M. J. Cheng, and J. J. Chen, Chem. Nat. Compd., 54, 1044 (2018).
S. Z. Shang, J. L. Shi, J. G. Tang, J. X. Jiang, W. Zhao, X. D. Zheng, P. Lei, J. M. Han, C. Y. Wang, D. L. Yuan, G. Y. Yang, Y. K. Chen, and M. M. Miao, Nat. Prod. Res., 33, 157 (2019).
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).
B. Sun, Y. X. Tian, F. Zhang, Q. Chen, Y. Zhang, Y. Luo, X. R. Wang, F. C. Lin, J. Yang, and H. R. Tang, Biomolecules, 8, 114 (2018).
X. Wang, L. J. Huang, M. J. Liang, Y. K. Li, W. L. Zeng, H. Y. Xiang, J. Li, X. Liu, Q. L. Mi, Y. D. Guo, G. Y. Yang, L. Deng, and Q. Gao, Chem. Nat. Compd., 56, 848 (2020).
L. J. Huang, X. Wang, M. J. Liang, Y. K. Li, W. S. Kong, X. Liu, H. Y. Xiang, Q. Gao, Q. L. Mi, L. Deng, G. Y. Yang, Y. D. Guo, and J. Li, Chem. Nat. Compd., 56, 1055 (2020).
L. J. Zhu, D. Luo, N. Lv, Y. K. Li, Q. L. Mi, J. Wang, W. S. Kong, Q. Gao, G. P. Li, G. Y. Yang, Q. F. Hu, Y. Guan, and Y. Q. Ye, Chem. Nat. Compd., 56, 806 (2020).
C. B. Liu, Q. P. Shen, Y. Wang, F. M. Zhang, P. He, X. X. Si, K. M. Wang, R. Z. Zhu, N. J. Xiang, and Z. H. Liu, Chem. Nat. Compd., 52, 992 (2016).
S. Saeed, W. U. Khan, S. U. Khan, M. Kamran, and K. H. Jung, Int. J. Mol. Sci., 21, 5665 (2020).
H. B. Huang, T. T. Cui, L. L. Zhang, Q. Y. Yang, Y. Yang, K. B. Xie, C. C. Fan, and Y. M. Zhou, Theor. Appl. Genet., 133, 2401 (2020).
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).
F. M. Dean and M. L. Robinson, Phytochemistry, 10, 3221 (1971).
Y. H. Kuo and B. Y. Lin, Chem. Pharm. Bull., 47, 428 (1999).
P. Li, W. L. Zeng, J. Li, T. D. Zhang, L. Ye, X. Liu, X. M. Li, C. B. Liu, M. Zhou, G. Y. Yang, F. M. Zhang, and Q. F. Hu, Chem. Nat. Compd., 55, 809 (2019).
Q. F. Hu, J. Wang, Y. Xu, Q. L. Mi, Y. K. Li, W. L. Zeng, Q. Gao, C. M. Song, H. T. Huang, H. Y. Xiang, X. M. Li, and G. Y. Yang, Heterocycles, 98, 444 (2019).
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).
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).
Acknowledgment
This work was supported financially by the Foundation of Yunnan basic research program (2019FD086), the Foundation of Yunnan Tobacco Industry Co., Ltd. (2018JC07), the high-tech projects of Yunnan Province (2017ZE027), and the Yunnan Innovative Research Team for Discovery and Comprehensive Utilization of Functional Small Molecules in Medicinal Plants (Grant to Q.H.).
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Published in Khimiya Prirodnykh Soedinenii, No. 6, November–December, 2021, pp. 874–877.
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Zhou, T., Yang, FX., Cai, BB. et al. Anti-Tobacco Mosaic Virus Chromone Derivatives from the Stems of Nicotiana tabacum. Chem Nat Compd 57, 1019–1022 (2021). https://doi.org/10.1007/s10600-021-03540-6
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DOI: https://doi.org/10.1007/s10600-021-03540-6