Using scalarane sesterterpenes to examine a sponge taxonomic anomaly

Journal of Natural Products

Volumn 60, Issue 6, 1997, Pages 556-561

  Jaspars, Marcel ^a   Jackson, Eric ^a   Lobkovsky, Emil ^b   Clardy, Jon ^b   Diaz, M Cristina ^a   Crews, Phillip ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b Department of Population Medicine and Diagnostic Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

20 DEOXO 20,22 DIMETHYL 3 OXOSCALARIN; 20 DEOXO 3 HYDROXY 20,22 DIMETHYLSCALARIN; SCALARANE; SESTERTERPENE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION; TAXONOMY; X RAY ANALYSIS;

ANIMALS; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; PORIFERA; TERPENES;

CARTERIOSPONGIA; DYSIDEA; PHYLLOSPONGIA; PORIFERA;

EID: 0030943553     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np960147x     Document Type: Article

References (31)

1. (a) Bergquist, P. R. N. Z. J. Zool. 1980, 7, 443-503.
2. (b) Bergquist, P. R.; Ayling, A. M.; Wilkinson, C. R. Pubbl. Stn. Zool. Napoli I. Marine Ecol. 1988, 9, 291-319.
3. Crews, P.; Naylor, S. In Progress in the Chemistry of Organic Natural Products; Herz, W., Grisebach, H., Kirby, G. W., Tamm, Ch., Eds.; Springer-Verlag: New York, 1985; Vol. 48, pp 203-269.
4. Hanson, J. R. Nat. Prod. Rep. 1986, 3, 123-132.
5. Alvi, K. A.; Crews, P. J. Nat. Prod. 1992, 55, 859-865.
6. Rao, Ch. B.; Kalidini, R. S. H. S. N.; Trimurtulu, B.; Rao, D. V. J. Nat. Prod. 1992, 54, 364-371.
7. Kazalauskas, R.; Murphy, P. T.; Wells, R. J. Aust. J. Chem. 1982, 35, 51-59.
8. Kazlauskas, R.; Murphy, P. T.; Wells, R. J.; Daly, J. J. Aust. J. Chem. 1980, 33, 1783-1797.
9. Barron, P. F.; Quinn, R. J.; Tucker, D. J. Aust. J. Chem. 1991, 44, 995-999.
10. Bowden, B. F.; Coll, J. C.; Li, H.; Cambie, R. C.; Kernan, M. R.; Bergquist, P. R. J. Nat. Prod. 1992, 55, 1234-1240.
11. Zeng, L.; Fu, X.; Su, J.; Pordesimo, E. O.; Traeger, S. C.; Schmitz, F. J. J. Nat. Prod. 1991, 54, 421-427.
12. Kitagawa, I.; Kobayashi, M.; Lee, N. K.; Oyama, Y.; Kyogoku, Y. Chem. Pharm. Bull. 1989, 37, 2078-2082.
13. Bergquist, P. R. Mem. Queensl. Mus. 1995, 38, 1-51.
14. Kashman, Y.; Zviely, M. Tetrahedron Lett. 1979, 3879-3882.
15. Higa, T.; Tanaka, J.; Kitamura, A.; Koyama, T.; Takahashi, M.; Uchida, T. Pure Appl. Chem. 1994, 66, 2227-2230.
16. Crews, P.; Jiménez, C.; O'Neil-Johnson, M. Tetrahedron 1991, 47, 3585-3600.
17. Hochlowski, J. E.; Faulkner, D. J.; Bass, L. J.; Clardy, J. J. Org. Chem. 1983, 48, 1738-1740.
18. Cimino, G.; De Stefano, S.; Minale, L. J. Chem. Soc., Perkin Trans. I 1977, 1587-1593.
19. Bax, A.; Subramanian, S. J. Magn. Reson. 1986, 67, 565-569.
20. Bax, A.; Summers, M. J. J. Am. Chem. Soc. 1986, 108, 2093-2094.
21. Braekman, J. C.; Daloze, D. Pure Appl. Chem. 1986, 58, 357-364.
22. Crews, P.; Kho-Wiseman, E. Tetrahedron Lett. 1978, 28, 2483-2486.
23. Boyd, M. R.; Paull, K. D. Drug Dev. Res. 1995, 34, 91-109.
24. Shoji, N.; Umeyama, A.; Motoki, S.; Arihara, S.; Ishida, T; Nomoto, K.; Kobayashi, J.; Takei, M. J. Nat. Prod. 1992, 55, 1682-1685.
25. Vacelet, J.; Boury-Esnalult, N.; De Vos, L.; Donadey, C. J. Morphol. 1989, 201, 119-129.
26. Bergquist, P. R.; Wells, R. W. In Marine Natural Products; Scheuer, P. J., Ed.; Academic Press: New York, 1983; pp 1-50.
27. Lendenfeld, R. A Monography of the Horny Sponges; London, 1889.
28. Jaspars, M.; Rail, T.; Laney, M.; Schatzman, R. C.; Diaz, M. C.; Schmitz, F. J.; Pordesimo, E. O.; Crews, P. Tetrahedron 1994, 50, 7367-7373.
29. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467-468.
30. Sheldrick, G. M. SHELX 93. Program for the refinement of crystal structures, University of Gottingen, Germany.
31. Atomic coordinates, bond distances and angles, and torsional angles for 2 have been deposited with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from Dr. Olga Kennard, University Chemical Laboratory, 12 Union Road, Cambridge CB2 1EZ, UK.