Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata

doi:10.1007/s13659-017-0140-z

Natural Products and Bioprospecting ›› 2017, Vol. 7 ›› Issue (5): 405-411.DOI: 10.1007/s13659-017-0140-z

• Original articles • Previous Articles Next Articles

Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata

Yu-Chen Liu^1,2, Zhi-Jun Zhang^1,2, Jia Su¹, Li-Yan Peng¹, Lu-Tai Pan³, Xing-De Wu¹, Qin-Shi Zhao¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100039, People's Republic of China;
3. Guiyang College of Traditional Chinese Medicine, Guiyang, People's Republic of China

Received:2017-05-07 Revised:2017-07-11 Online:2018-02-06 Published:2017-10-24
Supported by:
This work was financially supported by the NSFC-Joint Foundation of Yunnan Province (No. U1502223), the National Natural Science Foundation of China (No. 21402212), the Science and Technology Program of Yunnan province (No 2015FB173), and the CAS "Light of West China" Program and Youth Innovation Promotion Association CAS (X.D. Wu).

Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata

Yu-Chen Liu^1,2, Zhi-Jun Zhang^1,2, Jia Su¹, Li-Yan Peng¹, Lu-Tai Pan³, Xing-De Wu¹, Qin-Shi Zhao¹

1. State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, People's Republic of China;
2. University of Chinese Academy of Sciences, Beijing 100039, People's Republic of China;
3. Guiyang College of Traditional Chinese Medicine, Guiyang, People's Republic of China

通讯作者: Xing-De Wu,e-mail:wuxingde@mail.kib.ac.cn;Qin-Shi Zhao,e-mail:qinshizhao@mail.kib.ac.cn
基金资助:
This work was financially supported by the NSFC-Joint Foundation of Yunnan Province (No. U1502223), the National Natural Science Foundation of China (No. 21402212), the Science and Technology Program of Yunnan province (No 2015FB173), and the CAS "Light of West China" Program and Youth Innovation Promotion Association CAS (X.D. Wu).

Abstract

Abstract: Three new lycodine-type Lycopodium alkaloids, namely 1-methyllycodine (1), 8α-hydroxy-15,16-dehydro-des-N-methyl-α-obscurine (2), N-methyl-16-hydroxyhuperzine B (3), and one new natural lycodine-type Lycopodium alkaloid, N-methylhuperzine A (4), along with 11 known analogues (5-15), were isolated from the whole plants of club moss Huperzia serrata. The structures of 1-4 were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Among them, compound 1 was the first lycodine-type alkaloid possessing a methyl group at C-1. In addition, the structure of 5 was confirmed by the single-crystal X-ray crystallography data and its ¹³C NMR was reported for the first time in current study. Compounds 1-5 were tested their BACE1 inhibitory activity.

Key words: Lycopodium alkaloids, Lycodine-type, Huperzia serrata, BACE1 inhibitory activity

摘要： Three new lycodine-type Lycopodium alkaloids, namely 1-methyllycodine (1), 8α-hydroxy-15,16-dehydro-des-N-methyl-α-obscurine (2), N-methyl-16-hydroxyhuperzine B (3), and one new natural lycodine-type Lycopodium alkaloid, N-methylhuperzine A (4), along with 11 known analogues (5-15), were isolated from the whole plants of club moss Huperzia serrata. The structures of 1-4 were elucidated on the basis of NMR spectroscopic and mass spectrometry data. Among them, compound 1 was the first lycodine-type alkaloid possessing a methyl group at C-1. In addition, the structure of 5 was confirmed by the single-crystal X-ray crystallography data and its ¹³C NMR was reported for the first time in current study. Compounds 1-5 were tested their BACE1 inhibitory activity.

关键词: Lycopodium alkaloids, Lycodine-type, Huperzia serrata, BACE1 inhibitory activity

Yu-Chen Liu, Zhi-Jun Zhang, Jia Su, Li-Yan Peng, Lu-Tai Pan, Xing-De Wu, Qin-Shi Zhao. Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata[J]. Natural Products and Bioprospecting, 2017, 7(5): 405-411.

Yu-Chen Liu, Zhi-Jun Zhang, Jia Su, Li-Yan Peng, Lu-Tai Pan, Xing-De Wu, Qin-Shi Zhao. Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata[J]. 应用天然产物, 2017, 7(5): 405-411.

References

1. P. Siengalewicz, J. Mulzer, U. Rinner, Alkaloids 72, 1-151 (2013)
2. J.S. Liu, Y.L. Zhu, C.M. Yu, Y.Z. Zhou, Y.Y. Han, F.W. Wu, B.F. Qi, Can. J. Chem. 64, 837-839 (1986)
3. Y. Hirasawa, T. Tanaka, K. Koyama, H. Morita, Tetrahedron Lett. 50, 4816-4819 (2009)
4. Y. Hirasawa, J.I. Kobayashi, H. Morita, Heterocycles 77, 679-729 (2009)
5. X. Ma, R. Gang, David. Nat. Prod. Rep. 21, 752-772 (2004)
6. M. Kitajima, H. Takayama, Top. Curr. Chem. 309, 1-32 (2012)
7. W.A. Ayer, Nat. Prod. Rep. 8, 455-463 (1991)
8. Y. Tang, Y. Fu, J. Xiong, M. Li, G.L. Ma, G.X. Yang, B.G. Wei, Y. Zhao, H.Y. Zhang, J.F. Hu, J. Nat. Prod. 76, 1475-1484 (2013)
9. J.S. Liu, C.M. Yu, Y.Z. Zhou, Y.Y. Han, B.F. Qi, Y.L. Zhu, Acta Chem. Sin. 44, 1035-1040 (1986)
10. S. Shu, X. Zhao, W. Wang, G. Zhang, A. Cosoveanu, Y. Ahn, M. Wang, World J. Microbiol. Biotechnol. 30, 3101-3109 (2014)
11. H.B. Wang, C.H. Tan, J.J. Tan, S.J. Qu, Y.L. Chen, Y.M. Li, S.H. Jiang, D.Y. Zhu, Nat. Prod. Res. 23, 1363-1366 (2009)
12. C.H. Tan, B.D. Wang, S.H. Jiang, D.Y. Zhu, Planta Med. 68, 188-190 (2002)
13. C.H. Tan, S.H. Jiang, D.Y. Zhu, P. Huperzine, Tetrahedron Lett. 41, 5733-5736 (2000)
14. W.W. Jiang, F. Liu, X. Gao, J. He, X. Cheng, L.Y. Peng, X.D. Wu, Q.S. Zhao, Fitoterapia 99, 72-77 (2014)
15. Y.M. Ying, X.S. Liu, C.P. Tong, J.W. Wang, Z.J. Zhan, W.G. Shan, Helv. Chim. Acta 97, 1433-1439 (2014)
16. W.A. Ayer, L.M. Browne, H. Orszanska, Z. Valenta, J. Liu, Can. J. Chem. 67, 1538-1540 (1989)
17. F. Liu, X.D. Wu, J. He, X. Deng, L.Y. Peng, H.R. Luo, Q.S. Zhao, Tetrahedron Lett. 54, 4555-4557 (2013)
18. S.Q. Yuan, T.T. Wei, Yaoxue Xuebao 23, 516-520 (1988)
19. F.A.L. Anet, C.R. Eves, Can. J. Chem. 36, 902-909 (1958)
20. W.A. Ayer, G.G. Iverach, Can. J. Chem. 38, 1823-1826 (1960)
21. T.T.S. Nakashima, P. Peter, L.M. Browne, W.A. Ayer, Can. J. Chem. 53, 1936-1942 (1975)
22. C.Y. Choo, Y. Hirasawa, C. Karimata, K. Koyama, M. Sekiguchi, J.I. Kobayashi, H. Morita, Bioorg. Med. Chem. 15, 1703-1707 (2007)
23. W.A. Ayer, G.C. Kasitu, Can. J. Chem. 67, 1077-1086 (1989)
24. Y.C. Shen, C.H. Chen, J. Nat. Prod. 57, 824-826 (1994)
25. D.B. Zhang, J.J. Chen, Q.Y. Song, L. Zhang, K. Gao, Molecules 19, 9999-10010 (2014)
26. Y. Niu, H. Gao, F. Xu, C. Wang, P. Liu, G. Yang, Q. Sun, P. Xu, Chem. Biol. Drug Des. 80, 775-780 (2012)
27. S.N. Alam, K.A.H. Adams, D.B. MacLean, Can. J. Chem. 42, 2456-2466 (1964)
28. P.C. May, R.A. Dean, S.L. Lowe, F. Martenyi, S.M. Sheehan, L.N. Boggs, S.A. Monk, B.M. Mathes, D.J. Mergott, B.M. Watson, S.L. Stout, D.E. Timm, E. Smith Labell, C.R. Gonzales, M. Nakano, S.S. Jhee, M. Yen, L. Ereshefsky, T.D. Lindstrom, D.O. Calligaro, P.J. Cocke, D. Greg Hall, S. Friedrich, M. Citron, J.E. Audia, J. Neurosci. 31, 16507-16516 (2011)

Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata

Lycodine-Type Lycopodium Alkaloids from the Whole Plants of Huperzia serrata

PDF (PC)

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 1

Recommended Articles

Metrics

Comments