Lycojapodine A, a novel alkaloid from Lycopodium japonicum

Organic Letters

Volumn 11, Issue 6, 2009, Pages 1397-1400

  He, Juan ^a,b   Chen, Xuan Qin ^a   Li, Ming Ming ^a   Zhao, Yu ^a   Xu, Gang ^a   Cheng, Xiao ^a   Peng, Li Yan ^a   Xie, Min Jin ^c   Zheng, Yong Tang ^d   Wang, Yi Ping ^e   Zhao, Qin Shi ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c YUNNAN UNIVERSITY   (China)

^d KUNMING INSTITUTE OF ZOOLOGY   (China)

^e SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; CHOLINESTERASE INHIBITOR; HERBACEOUS AGENT; HUPERZINE A; LYCOJAPODINE A; SESQUITERPENE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; HUMAN IMMUNODEFICIENCY VIRUS 1; ISOLATION AND PURIFICATION; LYCOPODIUM; MEDICINAL PLANT; NUCLEAR MAGNETIC RESONANCE;

ALKALOIDS; ANTI-HIV AGENTS; CHOLINESTERASE INHIBITORS; DRUGS, CHINESE HERBAL; HIV-1; LYCOPODIUM; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANTS, MEDICINAL; SESQUITERPENES;

EID: 64049105024     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900079t     Document Type: Article

References (35)

1. Ma, X. Q.; Gang, D. R. Nat. Prod. Rep. 2004, 21, 752-772.
2. (a) Hirasawa, Y.; Kobayashi, J.; Morita, H. Org. Lett. 2006, 8, 123-126.
3. (b) Hirasawa, Y.; Morita, H.; Kobayashi, J. Org. Lett. 2004, 6, 3389-3391.
4. (c) Hirasawa, Y.; Morita, H.; Shiro, M.; Kobayashi, J. Org. Lett. 2003, 5, 3991-3993.
5. (d) Takayama, H.; Katakawa, K.; Kitajima, M.; Seki, H.; Yamaguchi, K.; Aimi, N. Org. Lett. 2001, 3, 4165-4167.
6. (e) Zhang, H. Y.; Zheng, C. Y.; Yan, H.; Wang, Z. F.; Tang, L. L.; Gao, X.; Tang, X.; Tang, X. C. Chem. Biol. Interact. 2008, 175, 396-402.
7. (f) Ishiuchi, K.; Kubota, Takaaki, T.; Mikami, Y.; Obara, Y.; Nakahata, N.; Kobayashi, J. Bioore. Med. Chem. 2007, 15, 413-417.
8. (g) Choo, C. Y.; Hirasawa, Y.; Karimata, C.; Koyama, K.; Sekiguchi, M.; Kobayashi, J.; Morita, H. Bioorg. Med. Chem. 2007, 15, 1703-1707.
9. (h) Ishiuchi, K.; Kubota, T.; Hoshino, T.; Obara, Y.; Nakahata, N.; Kobayashi, J. Bioorg. Med. Chem. 2006, 14, 5995-6000.
10. (i) Ishiu, K.; Kubota, T.; Morita, H.; Kobayashi, J. Tetrahedron Lett 2006, 47, 3287-3289, and references therein.
11. (a) Liu, K. M.; Chau, C. M.; Sha, C. K. Chem. Commun. 2008, 91, 91-93.
12. (b) Kozak, J. A.; Dake, G. R. Angew. Chem., Int. Ed. 2008, 47, 4221-3.
13. (c) Linghu, X.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2007, 46, 1-4.
14. Nishikawa, Y.; Kitajima, M.; Takayama, H. Org. Lett. 2008, 10, 1987-1990.
15. Nilsson, B. L.; Overman, L. E.; de Alaniz, J. R.; Mohde, J. M. J. Am. Chem. Soc. 2008, 130, 11297-11299.
16. Bisai, A.; West, S. P.; Sarpong, R. J. Am. Chem. Soc. 2008, 130, 7222-7223.
17. Institum Botanicum Kunmingense Academyiae Sinicae Edita, Flora Yunnanica; Sciences Press: Beijing, 2006; p 24.
18. (a) Wu, L.; Lu, Y.; Zheng, Q.-T.; Li, X.-L. Acta Crystalloer., Sect. E 2006, E62, o3269-o3270.
19. (b) Li, X. L.; Zhao, Y.; Cheng, X.; Tu, L.; Peng, L. Y.; Xu, G.; Zhao, Q. S. Helv. Chim. Acta 2006, 89, 1467-1473.
20. (c) Yan, J.; Zhang, X. M.; Li, Z.; Chen, J. C.; Sun, L. R.; Qiu, M. H. Helv. Chim. Acta 2005, 88, 240-244.
21. (d) Yan, J.; Sun, L. R.; Zhang, X. M.; Qiu, M. H. Heterocvcles 2005, 65, 661-666.
22. (e) Cai, X.; Pan, D. J.; Chen, Y. S.; Wu, W. L.; Liu, X. Z. Shanghai Yike Daxue Xuebao 1991, 18, 383-385.
23. Sun, Y.; Yan, J.; Meng, H.; He, C. L.; Yi, P.; Qiao, Y.; Qin, M. H. Helv. Chim. Acta 2008, 91, 2107-2109.
24. (a) Hiromitsu, T.; Kazuaki, K.; Mariko, K.; Kontaro, Y.; Norio, A. Tetrahedron Lett. 2002, 43, 8307-8311.
25. (b) Inubushi, Y.; Harayama, T. Chem. Pharm. Bull. 1981, 54, 1548-1562.
26. Hiromitsu, T.; Kazuaki, K.; Mariko, K.; Kontaro, Y.; Norio, A. Tetrahedron Lett. 2002, 43, 8307-8311.
27. (a) Braekman, J. C.; Nyembo, L.; Bourdoux, P.; Kahindo, N.; Hootele, C. Phytochemistry 1974, 13, 2519-2525.
28. (b) Wang, B. D.; Wang, J.; Sun, H. F.; Zhu, D. Y. Youjihuaxue 2001, 21, 606-610.
29. 3 calcd 278.1756).
30. 2 = 0.0925. The crystal structure of 1 was solved by direct method SHLXS-97 (Sheldrick, 1990) and expanded using difference Fourier technique, refined by the program SHLXL-97 (Sheldrick, 1997) and the full-matrix least-squares calculations. Crystallographic data for the structure of 1 have been deposited in the Cambridge Crystallographic Data Centre (deposition number CCDC 661199). Copies of these data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, U. K.; fax: (+44) 1223-336-033; or desposit@ccdc.cam.ac.uk).
31. Ayer, W. A.; Altenkirk, B.; Fukazawa, Y. Tetrahedron 1974, 30, 4213-4114.
32. (a) Smith, G. G.; Yates, B. L. J. Org. Chem. 1965, 30, 2067-2068.
33. (b) Shulman, H.; Makarov, C.; Ogawa, A. K.; Romesberg, F.; Keinan, E. J. Am. Chem., Soc. 2000, 8, 10743-10753.
34. Liu, I; Zhang, H. Y.; Tang, X. C.; Wang, B.; He, X. C.; Bai, D. L. Acta Pharamcol. Sin. 1998, 19 (5), 413-416.
35. Niu, X. M; Li, M. L.; Zhao, Q. S.; Na, Z.; Wang, S. J.; Lin, Z. W.; Sun, H. D. Plant Med. 2002, 68, 528-533.