A new fawcettimine-related alkaloid, 17α-methyllycoflexine (1), together with 14 known analogues, was isolated from the whole plants of Lycopodium japonicum Thunb. Their structures were established by extensive spectroscopic analysis, including NMR and HR-EI-MS experiments. Compound 1 is the second example of derivatives of lycoflexine with an unprecedented additional methyl group at C-17. All the isolated alkaloids were assayed for α-glucosidase inhibitory activity. Only lycodine showed weak α-glucosidase inhibitory activity, whereas the other alkaloids showed no activity.
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X. J. Wang, L. Li, S. S. Yu, S. G. Ma, J. Qu, Y. B. Liu, Y. Li, Y. Wang, and W. Tang, Fitoterapia, 91, 74 (2013).
H. Ishida, S. Kimura, N. Kogure, M. Kitajima, and H. Takayama, Tetrahedron, 71, 51 (2015).
A. S. Lee, B. B. Liau, and M. D. Shair, J. Am. Chem. Soc., 136, 13442 (2014).
P. Li, W. Huang, J. Zhuo, Z. Guo, W. Cao, L. Xu, L. Ma, Z. E. Chen, E. J. Kennelly, S. B. Wu, and C. Long, Tetrahedron, 71, 5308 (2015).
Y. Hirasawa, J. Kobayashi, and H. Morita, Heterocycles, 77, 679 (2009).
X. C. Zhang and L. B. Zhang, Flora of China, Science Press, Beijing, 6, 33 (2004).
H. Takayama, K. Katakawa, M. Kitajima, K. Yamaguchi, and N. Aimi, Tetrahedron Lett., 43, 8307 (2002).
Y. C. Liu, M. Fan, W. W. Jiang, F. Liu, X. D. Wu, J. He, X. Cheng, L. Y. Peng, J. Su, Z. J. Zhang, and Q. S. Zhao, J. Asian Nat. Prod. Res., 17, 967 (2015).
X. J. Wang, Y. B. Liu, L. Li, S. S. Yu, H. N. Lv, S. G. Ma, X. Q. Bao, D. Zhang, J. Qu, and Y. Li, Org. Lett., 14, 5688 (2012).
W. A. Ayer and G. C. Kasitu, Can. J. Chem., 67, 1077 (1989).
H. Liu and Y. Wang, China J. Chin. Mater. Med., 37, 475 (2012).
B. Li, W. D. Zhang, Y. R. He, L. Lu, D. Y. Kong, and Y. H. Shen, Chem. Pharm. Bull., 60, 1448 (2012).
F. W. Zhao, Q. Y. Sun, F. M. Yang, G. W. Hu, J. F. Luo, G. H. Tang, Y. H. Wang, and C. L. Long, Org. Lett., 12, 3922 (2010).
F. W. Zhao, Q. Y. Sun, F. M. Yang, J. F. Luo, G. W. Hu, F. Liu, Y. H. Wang, and C. L. Long, J. Braz. Chem. Soc., 23, 349 (2012).
L. B. Dong, X. Gao, F. Liu, J. He, X. D. Wu, Y. Li, and Q. S. Zhao, Org. Lett., 15, 3570 (2013).
K. Ishiuchi, T. Kubota, S. Hayashi, and J. Kobayashi, Tetrahedron Lett., 50, 6534 (2009).
D. B. Zhang, J. J. Chen, L. Zhang, Q. Y. Song, and K. Gao, Phytochem. Lett., 10, 76 (2014).
W. Y. Kang, L. Zhang, and Y. L. Song, China J. Chin. Mater. Med., 34, 406 (2009).
Acknowledgment
This investigation was supported by a Grant (No. 21162045) from the Natural Science Foundation of China and a Grant (No. 2009CC018) from Yunnan Province of China for basic research in social development.
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Published in Khimiya Prirodnykh Soedinenii, No. 4, July–August, 2018, pp. 617–618.
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Yang, Q., Zhu, Y., Zhan, R. et al. A New Fawcettimine-Related Alkaloid from Lycopodium japonicum. Chem Nat Compd 54, 729–731 (2018). https://doi.org/10.1007/s10600-018-2456-2
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DOI: https://doi.org/10.1007/s10600-018-2456-2