Furan-2-Carboxylic Acids from the Roots of Nicotiana tabacum and their Bioactivities
Two new furan-2-carboxylic acids, 5-(3-hydroxy-5-(hydroxymethyl)-4-methoxyphenyl)-3-methylfuran-2-carboxylic acid (1) and 5-(4-hydroxy-5-methoxy-2-methylphenyl)-3-methylfuran-2-carboxylic acid (2), together with two known furan-2-carboxylic acids (3 and 4) were isolated from the roots 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-tobacco mosaic virus (TMV) and cytotoxicity activities. The results revealed that compounds 1 and 2 showed high anti-TMV activity with inhibition rate of 35.8 and 32.6%. These rates are close to that of positive control. Compounds 1 and 2 also showed moderate to weak inhibitory activities against some tested human tumor cell lines with IC50 values in the range of 1.5–6.0 μM.
Keywordsfuran-2-carboxylic acid Nicotiana tabacum anti-tobacco mosaic virus activities cytotoxicity activities
This project was supported by the National Natural Science Foundation of China (Nos. 21302164, 31460144, and 21562044) and the Applied Fundamental Foundation of Yunnan Province (No. 2013FB097).
- 1.The Editorial Committee of the Administration Bureau of Flora of China, Flora of China, Vol. 67, Beijing Science and Technology Press, Beijing, 2005, p. 152.Google Scholar
- 3.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
- 5.X. Feng, Xin, J. S. Wang, J. Luo, and L. Y. Kong, J. Asian Nat. Prod. Res., 12, 252 (2010).Google Scholar
- 6.Y.-K. Chen, C.-Y. Meng, Z.-B. Su, L. Wang, G.-Y. Yang, and M.-M. Miao, Asian J. Chem., 26, 2246 (2014).Google Scholar
- 22.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
- 24.C. B. Liu, X. M. Xu, Q. P. Shen, W. Zhang, X. F. Shen, Y. K. Yang, F. M. Zhang, P. He, X. X. Si, Y. D. Guo, J. J. Xia, and G. Y Yang, Heterocycles, 92, 1095 (2016).Google Scholar