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Lycopodine-Type Alkaloids from Lycopodium japonicum |
| Juan He, Xing-De Wu, Fei Liu, Yu-Cheng Liu, Li-Yan Peng, Yu Zhao, Xiao Cheng, Huai-Rong Luo, Qin-Shi Zhao |
| State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China |
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Abstract Three new lycopodine-type alkaloids, 4α-hydroxyanhydrolycodoline(1), 4α, 6α-dihydroxyanhydrolycodoline(2), and 6-epi-8β-acetoxylycoclavine(3), and an artifact, lycoposerramine G nitrate(4), along with seventeen related known compounds, were isolated from the club moss Lycopodium japonicum Thunb. ex Murray(Lycopodiaceae). Their structures were elucidated by extensive spectroscopic methods as well as X-ray analysis. Compounds 1-4 were evaluated for their acetylcholine esterase inhibitory activity.
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| Keywords
Lycopodium japonicum
Lycopodine-type alkaloids
4α-Hydroxyanhydrolycodoline
4α, 6α-Dihydroxyanhydrolycodoline
6-epi-8β-Acetoxylycoclavine
Lycoposerramine G nitr
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| Fund:This work was financially supported by the National Natural Science Foundation of China(Nos. 90813004 and U0932602) and the National Basic Research Program of China(973 Program No. 2011CB915503). |
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Issue Date: 11 February 2018
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1. N. Sizemore, S.D. Rychnovsky, Org. Lett. 16, 688-691 (2014)
2. L. Zhao, C. Tsukano, E. Kwon, Y. Takemoto, M. Hirama, Angew. Chem. 52, 1722-1725 (2013)
3. K. Bishayee, D. Chakraborty, S. Ghosh, N. Boujedaini, A.R. Khuda-Bukhsh, Eur. J. Pharm. 698, 110-121 (2013)
4. L.B. Dong, X. Gao, F. Liu, J. He, X.D. Wu, Y. Li, Q.S. Zhao, Org. Lett. 15, 3570-3573 (2013)
5. M.G. Vallejo, M.G. Ortega, J.L. Cabrera, A.M. Agnese, Tetrahedron Lett. 54, 5197-5200 (2013)
6. Y. Hirasawa, J. Kobayashi, H. Morita, Heterocycles 77, 679-729 (2009)
7. X.Q. Ma, D.R. Gang, R. Nat. Prod. Rep. 21, 752-772 (2004)
8. W.A. Ayer, Nat. Prod. Rep. 8, 455-663 (1991)
9. X.J. Wang, L. Li, S.S. Yu, S.G. Ma, J. Qu, Y.B. Liu, Y. Li, Y. Wang, W. Tang, Fitoterapia 91, 74-81 (2013)
10. X.J. Wang, L. Li, Y.K. Si, S.S. Yu, S.G. Ma, X.Q. Bao, D. Zhang, J. Qu, Y.B. Liu, Y. Li, Tetrahedron 69, 6234-6240 (2013)
11. X.J. Wang, Y.B. Liu, L. Li, S.S. Yu, H.N. Lv, S.G. Ma, X.Q. Bao, D. Zhang, J. Qu, Y. Li, Org. Lett. 14, 5688-5691 (2012)
12. X.L. Li, Y. Zhao, X. Cheng, L. Tu, L.Y. Peng, G. Xu, Q.S. Zhao, Helv. Chim. Acta 89, 1467-1473 (2006)
13. J. Yan, L. Sun, X. Zhang, M. Qiu, Heterocycles 65, 661-666 (2005)
14. X. Cai, D. Pan, Y. Chen, W. Wu, X. Liu, Shanghai Yike Daxue Xuebao 18, 383-385 (1991)
15. J. He, X.Q. Chen, M.M. Li, Y. Zhao, G. Xu, X. Cheng, L.Y. Peng, M.J. Xie, Y.T. Zheng, Y.P. Wang, Q.S. Zhao, Org. Lett. 11, 1397-1400 (2009)
16. Y.R. Yang, L. Shen, K. Wei, Q.S. Zhao, J. Org. Chem. 75, 1317-1320 (2010)
17. T.T. Nakashima, P.P. Singer, L.M. Browne, W.A. Ayer, Can. J. Chem. 53, 1936-1942 (1975)
18. H. Takayama, K. Katakawa, M. Kitajima, K. Yamaguchi, N. Aimi, Chem. Pharm. Bull. 51, 1163-1169 (2003)
19. W.A. Ayer, B. Altenkirk, S. Valverde-Lopez, B. Douglas, R.F. Raffauf, J.A. Weisbach, Can. J. Chem. 46, 15-20 (1968)
20. D.B. MacLean, Can. J. Chem. 41, 2654-2670 (1963)
21. H. Morita, M. Arisaka, N. Yoshida, J.I. Kobayashi, J. Org. Chem. 65, 6241-6245 (2000)
22. B.D. Wang, J. Wang, H.F. Sun, D.Y. Zhu, Chin. J. Org. Chem. 21, 606-610 (2001)
23. C.H. Tan, D.Y. Zhu, Helv. Chim. Acta 87, 1963-1967 (2004)
24. X.D. Wu, J. He, G. Xu, L.Y. Peng, L.D. Song, Q.S. Zhao, Acta Bot. Yunnan. 31, 93-96 (2009)
25. Y.F. Yang, S.J. Qu, K. Xiao, S.H. Jiang, J.J. Tan, C.H. Tan, D.Y. Zhu, J. Asian Nat. Prod. Res. 12, 1005-1009 (2010)
26. B. Li, W.D. Zhang, Y.R. He, L. Lu, D.Y. Kong, Y.H. Shen, Chem. Pharm. Bull. 60, 1448-1452 (2012)
27. G.L. Ellman, K.D. Courtney, V.J. Andres, R.M. Featherstone, Biochem. Pharmacol. 7, 88-95 (1961) |
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