Cupolamide A: A Cytotoxic Cyclic Heptapeptide from Two Samples of the Sponge Theonella cupola

Journal of Organic Chemistry

Volumn 62, Issue 22, 1997, Pages 7765-7767

  Bonnington, Lea S ^a   Tanaka, Junichi ^a   Higa, Tatsuo ^a   Kimura, Junji ^b   Yoshimura, Yuki ^b   Nakao, Yoichi ^c   Yoshida, Wesley Y ^c   Scheuer, Paul J ^c  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

^b AOYAMA GAKUIN UNIVERSITY   (Japan)

^c UNIVERSITY OF HAWAII   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001303726     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9710285     Document Type: Article

References (16)

1. Carmely, S.; Kashman, Y. Tetrahedron Lett. 1985, 26, 511-514.
2. Kobayashi, M.; Tanaka, J.; Katori, T.; Matsuura, M.; Yamashita, M.; Kitagawa, I. Chem. Pharm. Bull. 1990, 38, 2409-2418.
3. Sakemi, S.; Ichiba, T.; Kohmoto, S.; Saucy, G.; Higa, T. J. Am. Chem. Soc. 1988, 110, 4851-4853.
4. Matsunaga, S.; Fusetani, N.; Nakao, Y. Tetrahedron 1992, 48, 8369-8376.
5. Fusetani, N.; Matsunaga, S. Chem. Rev. 1993, 93, 1793-1806.
6. Ichiba, T.; Nakao, Y.; Scheuer, P. J.; Sata, N. U.; Kelly-Borges, M. Tetrahedron Lett. 1995, 36, 3977-3980.
7. At a seminar at the University of Hawai'i on April 4, 1997, one of the authors (T.H.) revealed the structure of cupolamide A, which appeared closely related to kumamide. Careful comparison of spectral data revealed their identity. According to T. Ichiba, collector of the Indonesian sponge, the two specimens possess identical morphology.
8. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.
9. Matsunaga, S.; Fusetani, N. J. Org. Chem. 1995, 60, 1177-1180.
10. Mauger, A. B. J. Nat. Prod. 1996, 59, 1205-1211.
11. Gerwick, W. H.; Jiang, Z. D.; Agarwal, S. K.; Farmer, B. T. Tetrahedron 1992, 48, 2313-2324.
12. Goetz, G.; Nakao, Y.; Scheuer, P. J. J. Nat. Prod. 1997, 60, 562-567.
13. Namikoshi, M.; Rinehart, K. L.; Sakai, R.; Sivonen, K.; Carmichael, W. W. J. Org. Chem. 1990, 55, 6135-6139.
14. Lim, Y.; Suh, J-W.; Kim, S.; Hyun, B.; Kim, C.; Lee, C-H. J. Antibiot. 1994, 47, 1406-1416.
15. Jacques, P.; Gwose, I.; Seinsche, D.; Taraz, K.; Budzikiewicz, H.; Schroeder, H.; Ongena, M.; Thonart, P. Nat. Prod. Lett. 1993, 3, 213-218.
16. Yamada, S.; Hongo, C.; Yoshioka, R.; Chibata, I. J. Org. Chem. 1983, 48, 843-846.