Uniquely modified imidazole alkaloids from a calcareous Leucetta sponge

Journal of Natural Products

Volumn 66, Issue 7, 2003, Pages 939-942

  Edrada, Ru Angelie ^a   Stessman, Chad C ^a   Crews, Phillip ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE; ALKALOID; CALCARIDINE A; FUNCTIONAL GROUP; IMIDAZOLE DERIVATIVE; SPIRO COMPOUND; SPIROCALCARIDINE A; SPIROCALCARIDINE B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHIRALITY; DRUG ISOLATION; DRUG STRUCTURE; LEUCETTA; METABOLITE; NONHUMAN; SPONGE (PORIFERA);

ALKALOIDS; ANIMALS; FIJI; IMIDAZOLES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; STEREOISOMERISM;

CALCAREA; INVERTEBRATA; LEUCETTA; LEUCETTA SP.; PORIFERA;

EID: 0041342052     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np020503d     Document Type: Article

References (24)

1. Faulkner, D. J. Nat. Prod. Rep. 2001, 18, 1-49, and previous entries in this series.
2. (a) Cardellina, J. H.; Meinwald, J. J. Org. Chem. 1981, 46, 4782-4784.
3. (b) Pfleiderer, W. Tetrahedron 1988, 44, 3373-3378.
4. (a) Alvi, K. A.; Crews, P.; Loughhead, D. G. J. Nat. Prod. 1991, 54, 1509-1515.
5. (b) Alvi, K. A.; Peters, B. M.; Hunter, L. M.; Crews, P. Tetrahedron 1993, 49, 329-336.
6. Carmely, K.; Kashman, Y. Tetrahedron Lett. 1987, 28, 3003-3006.
7. (a) Carmely, S.; Ilan, M.; Kashman, Y. Tetrahedron 1989, 45, 2193-2200.
8. (b) Crews, P.; Clark, D. P., Tenney, K. J. Nat. Prod. 2003, 66, 177-182.
9. (a) Akee, R. K.; Carroll, T. R.; Yoshida, W. Y.; Scheuer, P. J.; Stout, T. J.; Clardy, J. J. Org. Chem. 1990, 55, 1944-1946.
10. (b) Fu, X.; Barnes, J. R.; Do, T.; Schmitz, F. J. J. Nat. Prod. 1997, 60, 497-498.
11. (a) He, H.; Faulkner, D. J. J. Org. Chem. 1992, 57, 2176-2178.
12. (b) Mancini, I.; Guella, G.; Debitus, C.; Pietra, F. Helv. Chim. Acta 1995, 78, 1178-1184.
13. See underwater photograph of specimen 230 p 60: Colin, P. L.; Arneson, C. Tropical Invertebrates; Coral Reef Press: Beverly Hills, 1995; p 60.
14. For example see the underwater photographs of Leucetta sp. in: (a) Gosliner, T. M.; Behrens, D. W.; Williams, G. C. Coral Reef Animals of the Indo-Pacific; Sea Challengers: Monterey, 1996; entry no. 5, p 16. (b) Bertsch, H., Martin, K., Eds. Animal Life from Africa to Hawai'i Exclusive of the Vertebrates; Sea Challengers: Monterey 1996; p 16.
15. For example see the underwater photographs of Leucetta sp. in: (a) Gosliner, T. M.; Behrens, D. W.; Williams, G. C. Coral Reef Animals of the Indo-Pacific; Sea Challengers: Monterey, 1996; entry no. 5, p 16. (b) Bertsch, H., Martin, K., Eds. Animal Life from Africa to Hawai'i Exclusive of the Vertebrates; Sea Challengers: Monterey 1996; p 16.
16. Jaspars, M.; Rali, T.; Laney, M.; Schatzman, R. C.; Diaz, M. C. Schmitz, F. J.; Pordesimo, E. O.; Crews, P. Tetrahedron 1994, 50, 7367-7373.
17. Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. In Spectral Data for Structure Determination of Organic Compounds, 2nd ed.; Freisenius, W., Huber, J. F. K., Pungor, E., Rechnitz, G. A., Simon, W., West, T. S., Eds.; Springer-Verlag: Berlin, 1989; p C190.
18. Engstrom, K. Phytochemistry 1998, 49, 1585-1587.
19. (a) Patriana, C.; Fenical, W.; Cocoran, E.; Clardy, J. Tetrahedron Lett. 1993, 34, 3371-3372.
20. (b) Brennan, M. R.; Kim, I. K.; Erickson, K. L. J. Nat. Prod. 1993, 56, 76-84
21. Barrow, C. J.; Blunt, J. W.; Munro, M. H. G. Aust. J. Chem. 1988, 41, 1755-1761
22. DellGreca M.; Previtera, L.; Fiorentino, A.; Pinto, G.; Pollio, A. Tetrahedron 1996, 52, 13981-13990.
23. Jaspars, M.; Rali, T.; Laney, M.; Schatzman, R. C.; Diaz, M. C.; Schmitz, F. J.; Pordesimo, E. O.; Crews, P. Tetrahedron 1994, 50, 7367-7373.
24. See: "Spongeguide" available from Hooper, J.N.A.; www.qmuseum.qld.gov.au/organisation/sections/ SessileMarineInvertebrates/index.asp.