Lycospidine A, a new type of Lycopodium alkaloid from Lycopodium complanatum

Organic Letters

Volumn 15, Issue 10, 2013, Pages 2438-2441

  Cheng, Jin Tang ^a,b   Liu, Fei ^a,b   Li, Xiao Nian ^a   Wu, Xing De ^a   Dong, Liao Bin ^a,b   Peng, Li Yan ^a   Huang, Sheng Xiong ^a   He, Juan ^a   Zhao, Qin Shi ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; FUSED HETEROCYCLIC RINGS; LYCOSPIDINE A;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; LYCOPODIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ALKALOIDS; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; LYCOPODIUM; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE;

EID: 84877901161     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol400907v     Document Type: Article

References (51)

1. Hirasawa, Y.; Kobayashi, J.; Morita, H. Heterocycles 2009, 77, 679-729
2. Kobayashi, J.; Morita, H. The Alkaloids: Chemistry and Biology; Cordell, G. A., Ed.; Natural Products Inc.: Evanston, IL, 2005; Vol. 61, pp 1-57.
3. Ma, X. Q.; Gang, D. R. Nat. Prod. Rep. 2004, 752-772
4. Liu, J. S.; Zhu, Y. L.; Yu, C. M.; Zhou, Y. Z.; Han, Y. Y.; Wu, F. W.; Qi, B. F. Can. J. Chem. 1986, 64, 837-839
5. Nishimura, T.; Unni, A. K.; Yokoshima, S.; Fukuyama, T. J. Am. Chem. Soc. 2013, 135, 3243-3247
6. Newton, J. N.; Fischer, D. F.; Sarpong, R. Angew. Chem., Int. Ed. 2013, 52, 1726-1730
7. Bradshaw, B.; Luque-Corredera, C.; Bonjoch, J. Org. Lett. 2013, 15, 326-329
8. Li, H. H.; Wang, X. M.; Lei, X. G. Angew. Chem., Int. Ed. 2012, 51, 491-495
9. Hemscheidt, T.; Spenser, I. D. J. Am. Chem. Soc. 1996, 118, 1799-1800
10. Hemscheidt, T.; Spenser, I. D. J. Am. Chem. Soc. 1993, 115, 3020-3021
11. Marshall, W. D.; Nguyen, T. T.; MacLean, D. B.; Spenser, I. D. Can. J. Chem. 1975, 53, 41-50
12. Lu, S. G.; Zhang, G. F.; Su, W. H.; Wang, R. X.; Li, C. X.; Xu, C. D.; Deng, X. C.; Duan, Y. Q.; Wang, Y.; Zhang, B. B. Pteridology; Higher Education Press: Beijing, 2007; pp 45-47.
13. Wu, X. D.; He, J.; Xu, G.; Peng, L. Y.; Song, L. D.; Zhao, Q. S. Acta Botanica Yunnanica 2009, 31, 93-96
14. Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. J. Org. Chem. 2001, 66, 5901-5904
15. Kobayashi, J.; Hirasawa, Y.; Yoshida, N.; Morita, H. Tetrahedron Lett. 2000, 41, 9069-9073
16. Ishiuchi, K.; Kubota, T.; Morita, H.; Kobayashi, J. Tetrahedron Lett. 2006, 47, 3287-3289
17. Kobayashi, J.; Ishiuchi, K.; Kubota, T.; Hayashi, S.; Shibata, T. Tetrahedron Lett. 2009, 50, 6534-6536
18. He, J.; Chen, X. Q.; Li, M. M.; Zhao, Y.; Xu, G.; Cheng, X.; Peng, L. Y.; Xie, M. J.; Zheng, Y. T.; Wang, Y. P.; Zhao, Q. S. Org. Lett. 2009, 11, 1397-1400
19. Dong, L. B.; Yang, J.; He, J.; Luo, H. R.; Wu, X. D.; Deng, X.; Peng, L. Y.; Zhao, Q. S. Chem. Commun. 2012, 48, 9038-9040
20. Yang, Y. F.; Qu, S. J.; Xiao, K.; Jiang, S. H.; Tan, J. J.; Tan, C. H.; Zhu, D. Y. J. Asian Nat. Prod. Res. 2010, 12, 1005-1009
21. Hirasawa, Y.; Kato, E.; Kobayashi, J.; Kawahara, N.; Goda, Y.; Shiro, M.; Morita, H. Bioorg. Med. Chem. 2008, 16, 6167-6171
22. Choo, C. Y.; Hirasawa, Y.; Karimata, C.; Koyama, K.; Sekiguchi, M.; Kobayashi, J.; Morita, H. Bioorg. Med. Chem. 2007, 15, 1703-1707
23. Yin, S.; Fan, C. Q.; Wang, X. N.; Yue, J. M. Helv. Chim. Acta 2006, 89, 138-143
24. Tan, C. H.; Chen, G. F.; Ma, X. Q.; Jiang, S. H.; Zhu, D. Y. J. Nat. Prod. 2002, 65, 1021-1022
25. Liu, J. S.; Huang, M. F. Phytochemistry 1994, 37, 1759-61
26. Hu, P.; Gross, M. L.; Yuan, S. Q.; Wei, T. T.; Lu, Y. Q. Org. Mass Spectrom. 1992, 27, 99-104
27. Miao, Z.; Yang, Z.; Lu, Y.; Liang, X. Acta Chim. Sin. 1989, 47, 702-704
28. Ayer, W. A.; Browne, L. M.; Orszanska, H.; Valenta, Z.; Liu, J. Can. J. Chem. 1989, 67, 1538-1540
29. Valenta, Z.; Yoshimura, H.; Rogers, E. F.; Ternbah, M.; Wiesner, K. Tetrahedron Lett. 1960, 10, 26-33
30. 2 = 0.0970. The crystal structure of 1 was solved by direct method SHLXS-97 (Sheldrick, 1990). Crystallographic data for the structure of 1 have been deposited in the Cambridge Crystallographic Data Centre (deposition number: CCDC 931623). 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, UK.; fax: (+44) 1223-336-033; or desposit@ccdc.cam.ac.uk).
31. Castillo, M.; Gupta, R. N.; Ho, Y. K.; MacLean, D. B.; Spenser, I. D. Can. J. Chem. 1970, 48, 2911-2918
32. Castillo, M.; Gupta, R. N.; Ho, Y. K.; MacLean, D. B.; Spenser, I. D. J. Am. Chem. Soc. 1970, 92, 1074-1075
33. Braekman, J. C.; Gupta, R. N.; MacLean, D. B.; Spenser, I. D. Can. J. Chem. 1972, 50, 2591-2602
34. Katakawa, K.; Kitajima, M.; Yamaguchi, K.; Takayama, H. Heterocycles 2006, 69, 223-229
35. Kubota, T.; Yahata, H.; Yamamoto, S.; Hayashi, S.; Shibata, T.; Kobayashi, J. Bioorg. Med. Chem. Lett. 2009, 19, 3577-3580
36. Ishiuchi, K.; Kubota, T.; Mikami, Y.; Obara, Y.; Nakahata, N.; Kobayashi, J. Bioorg. Med. Chem. 2007, 15, 413-417
37. Burnell, R. H.; Mootoo, B. S. Can. J. Chem. 1961, 39, 1090-1093
38. Morita, H.; Ishiuchi, K.; Haganuma, A.; Hoshino, T.; Obara, Y.; Nakahatab, N.; Kobayashi, J. Tetrahedron 2005, 61, 1955-1960
39. Burnell, R. H. J. Chem. Soc. 1959, 3091-3093
40. Katakawa, K.; Kogure, N.; Kitajima, M.; Takayama, H. Helv. Chim. Acta 2009, 92, 445-452
41. Ayer, W. A. Nat. Prod. Rep. 1991, 8, 455-463
42. Wang, X. J.; Zhang, G. J.; Zhuang, P. Y.; Zhang, Y.; Yu, S. S.; Bao, X. Q.; Zhang, D.; Yuan, Y. H.; Chen, N. H.; Ma, S. G.; Qu, J.; Li, Y. Org. Lett. 2012, 14, 2614-2617
43. Hirasawa, Y.; Kato, Y.; Wong, C. P.; Uchiyama, N.; Goda, Y.; Hadi, A. H. A.; Morita, H. Tetrahedron Lett. 2013, 54, 1593-1595
44. Ishiuchi, K. I.; Kubota, T.; Ishiyama, H.; Hayashi, S.; Shibata, T.; Kobayashi, J. I. Tetrahedron Lett. 2011, 52, 289-292
45. Hirasawa, Y.; Kobayashi, J.; Morita, H. Org. Lett. 2006, 8, 123-126
46. Wang, X. J.; Liu, Y. B.; Li, L.; Yu, S. S.; Lv, H. N.; Ma, S. G.; Bao, X. Q.; Zhang, D.; Qu, J.; Li, Y. Org. Lett. 2012, 14, 5688-5691
47. Zhao, F. W.; Sun, Q. Y.; Yang, F. M.; Hu, G. W.; Luo, J. F.; Tang, G. H.; Wang, Y. H.; Long, C. L. Org. Lett. 2010, 12, 3922-3925
48. Rhee, I. K.; Appels, N.; Hofte, B.; Karabatak, B.; Erkelens, C.; Stark, L. M.; Flippin, L. A.; Verpoorte, R. Biol. Pharm. Bull. 2004, 27, 1804-1809
49. Ellman, G. L.; Courtney, K. D.; Andres, V., jr; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88-95
50. Sun, Q.; Yang, F. Chem. Pharm. Bull. 2008, 24, 1387-1392
51. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.; Fine, D. L.; Abbott, B. J.; Mayo, J. G.; Shoemaker, R. H.; Boyd, M. R. Cancer Res. 1988, 48, 589-601