Hupermine A, a novel C16N2-type Lycopodium alkaloid from Huperzia phlegmaria

Tetrahedron Letters

Volumn 55, Issue 11, 2014, Pages 1902-1904

  Hirasawa, Yusuke ^a   Kato, Yuri ^a   Wong, Chin Piow ^a   Uchiyama, Nahoko ^b   Goda, Yukihiro ^b   Hadi, A Hamid A ^c   Ali, Hapipah Mohd ^c   Morita, Hiroshi ^a  

^a HOSHI UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^c UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Hupermine A; Huperzia phlegmaria; Lycopodium alkaloid; Lycopodium phlegmaria

Indexed keywords

ALKALOID; AMINE; ANTINEOPLASTIC AGENT; HUPERMINE A; INDUCIBLE NITRIC OXIDE SYNTHASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; HUPERZIA; HUPERZIA PHLEGMARIA; IC 50; LYCOPODIUM; MOUSE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

HUPERZIA PHLEGMARIA; LYCOPODIOPHYTA; LYCOPODIUM;

EID: 84896704626     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2014.01.141     Document Type: Article

References (28)

1. For reviews of the Lycopodium alkaloids, see: Y. Hirasawa, J. Kobayashi, and H. Morita Heterocycles 77 2009 679 729
2. J. Kobayashi, and H. Morita G.A. Cordell, The Alkaloids Vol. 61 2004 Academic Press New York 1
3. W.A. Ayer, and L.S. Trifonov G.A. Cordell, A. Brossi, The Alkaloids Vol. 45 1994 Academic Press New York 233
4. W.A. Ayer Nat. Prod. Rep. 8 1991 455 463
5. D.B. MacLean A. Brossi, The Alkaloids Vol. 26 1985 Academic Press New York 241
6. D.B. MacLean R.H.F. Manske, The Alkaloids Vol. 14 1973 Academic Press New York 348
7. D.B. MacLean R.H.F. Manske, The Alkaloids Vol. 10 1968 Academic Press New York 305
8. T. Hemscheidt, and I.D. Spenser J. Am. Chem. Soc. 118 1996 1799 1800
9. T. Hemscheidt, and I.D. Spenser J. Am. Chem. Soc. 115 1993 3020 3021
10. J.S. Liu, Y.L. Zhu, C.M. Yu, Y.Z. Zhou, Y.Y. Han, F.W. Wu, and B.F. Qi Can. J. Chem. 64 1986 837 839
11. B.B. Snider, and J.F. Grabowski J. Org. Chem. 72 2007 1039 1042
12. D.C. Beshore, and A.B. Smith III J. Am. Chem. Soc. 129 2007 4148 4149
13. S.M. Canham, D.J. France, and L.E. Overman J. Am. Chem. Soc. 132 2010 7876 7877
14. Y. Nakamura, A.M. Burke, S. Kotani, J.W. Ziller, and S.D. Rychnovsky Org. Lett. 12 2010 72 75
15. D.F. Fischer, and R. Sarpong J. Am. Chem. Soc. 132 2010 5926 5927
16. C. Yuan, C.-T. Chang, A. Axelrod, and D. Siegel J. Am. Chem. Soc. 132 2010 5924 5925 and references cited therein
17. A.P. Kozikowski, and W. Tueckmantel Acc. Chem. Res. 32 1999 641 650
18. D.L. Bai, X.C. Tang, and X.C. He Curr. Med. Chem. 7 2000 355 374
19. Y. Hirasawa, R. Matsuya, K. Shaari, N.H. Lajis, N. Uchiyama, Y. Goda, and H. Morita Tetrahedron Lett. 53 2012 3971 3973
20. Y. Hirasawa, A. Astulla, M. Shiro, and H. Morita Tetrahedron Lett. 52 2011 4216 4218
21. Y. Hirasawa, Y. Kato, C.P. Wong, N. Uchiyama, Y. Goda, A.H.A. Hadi, and H. Morita Tetrahedron Lett. 54 2013 1593 1595
22. Y. Hirasawa, T. Tanaka, K. Koyama, and H. Morita Tetrahedron Lett. 50 2009 4816 4819
23. Y. Hirasawa, E. Kato, J. Kobayashi, N. Kawahara, Y. Goda, M. Shiro, and H. Morita Bioorg. Med. Chem. 16 2008 6167 6171
24. H. Morita, Y. Hirasawa, T. Shinzato, and J. Kobayashi Tetrahedron 60 2004 7015 7023
25. J. Janar, A.E. Nugroho, C.P. Wong, Y. Hirasawa, T. Kaneda, O. Shirota, and H. Morita Chem. Pharm. Bull. 60 2012 154 159
26. F. Yamasaki, S. Machida, S. Nakata, A.E. Nugroho, Y. Hirasawa, T. Kaneda, O. Shirota, T. Sugizaki, N. Hagane, and H. Morita J. Nat. Med. 67 2013 212 216
27. J. Janar, L. Fang, C.P. Wong, T. Kaneda, Y. Hirasawa, B.G. Shahmanova, A.Z. Abduahitovich, and H. Morita Heterocycles 86 2012 1591 1595
28. T. Hoshino, M. Matsuda, Y. Yamashita, M. Takehara, M. Fukuya, K. Mineda, D. Maji, H. Ihn, H. Adachi, G. Sobue, Y. Funasaka, and T. Mizushuma J. Biol. Chem. 17 2010 13254 13263