Halichonadin F and the Cu(I) complex of halichonadin C from the sponge Halichondria sp.

Journal of Natural Products

Volumn 71, Issue 7, 2008, Pages 1301-1303

  Ishiyama, Haruaki ^a   Kozawa, Shingo ^a   Aoyama, Kazuki ^b   Mikami, Yuzuru ^b   Fromont, Jane ^c   Kobayashi, Jun'ichi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c WESTERN AUSTRALIAN MUSEUM   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

COPPER COMPLEX; HALICHONADIN C; HALICHONADIN F; SESQUITERPENOID;

ANTIMICROBIAL ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CRYPTOCOCCUS NEOFORMANS; HALICHONDRIA; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STEREOCHEMISTRY; TRICHOPHYTON MENTAGROPHYTES;

ANIMALS; COPPER; JAPAN; MARINE BIOLOGY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; SESQUITERPENES, EUDESMANE;

HALICHONDRIA;

EID: 49049101890     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np800164s     Document Type: Article

References (17)

1. Wright, A. D.; Köning, G. M. J. Nat. Prod. 1996, 59, 710-716.
2. (a) Faulkner, D. J. Nat. Prod. Rep. 1984, 1, 551-598.
3. (b) Faulkner, D. J. Nat. Prod. Rep. 1987, 4, 539-590.
4. (c) Edenborough, M. S.; Herbert, R. B. Nat. Prod. Rep. 1988, 5, 229-245.
5. Burreson, B. J.; Scheuer, P. J.; Finer, J.; Clardy, J. J. Am. Chem. Soc. 1975, 97, 4763-4764.
6. (a) Tsuda, M.; Endo, T.; Perpelescu, M.; Yoshida, S.; Watanabe, K.; Fromont, J.; Mikami, Y.; Kobayashi, J. Tetrahedron 2003, 59, 1137-1141.
7. (b) Endo, T.; Tsuda, M.; Okada, T.; Mitsuhashi, S.; Shima, H.; Kikuchi, K.; Mikami, Y.; Fromont, J.; Kobayashi, J. J. Nat. Prod. 2004, 67, 1262-1267.
8. Ishiyama, H.; Hashimoto, A.; Fromont, J.; Hoshino, Y.; Mikami, Y.; Kobayashi, J. Tetrahedron 2005, 61, 1101-1105.
9. Burgoyne, D. L.; Dumdei, E. J.; Andersen, R. J. Tetrahedron 1993, 49, 4503-4510.
10. Kozawa, S.; Ishiyama, H.; Fromont, J.; Kobayashi, J. J. Nat. Prod. 2008, 71, 445-447.
11. (a) Tada, H.; Yasuda, F. Chem. Pharm. Bull. 1985, 33, 1941-1945.
12. (b) da Silva, C. C.; Almagro, V.; Zukerman-Schpector, J.; Castellano, E. E.; Marsaioli, A. J. J. Org. Chem. 1994, 59, 2880-2881.
13. Gijsen, H. J. M.; Kanai, K.; Stork, G. A.; Wijnberg, J. B. P. A.; Orru, R. V. A.; Seelen, C. G. J. M.; van der Kerk, S. M.; de Groot, A. Tetrahedron 1990, 46, 7237-7246, and references therein.
14. Treatment of natural halichonadin C with CuI gave a trace of the Cu(I)-coordinated halichonadin C (2), although CuI rather than CuC1 has been used for formation of a Cu(I)-coordinated trimer of p-tolyl isocyanide.
15. Toth, A.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. J. Chem. Soc., Dalton Trans. 1988, 1599-1604.
16. Fattorusso, E.; Magno, S.; Mayol, L.; Santacroce, C.; Sica, D. Tetrahedron 1974, 30, 3911-3913.
17. Fattorusso, E.; Magno, S.; Mayol, L.; Santacroce, C.; Sica, D. Tetrahedron 1975, 31, 269-270.