Aciculitins A-C: Cytotoxic and antifungal cyclic peptides from the lithistid sponge Aciculites orientalis

Journal of the American Chemical Society

Volumn 118, Issue 18, 1996, Pages 4314-4321

  Bewley, Carole A ^a   He, Haiyin ^a   Williams, David H ^a   Faulkner, D John ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; CYCLOPEPTIDE;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; NONHUMAN; PEPTIDE ANALYSIS; SPONGE (PORIFERA);

EID: 15844411955     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja953628w     Document Type: Article

References (29)

1. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223 and previous reviews in this series.
2. Fusetani, N.: Matsunaga, S. Chem. Rev. 1993, 93, 1793.
3. Doi, M.: Ishida. T.; Kobayastii, M.: Kitagawa, I. J. Org. Chem. 1991, 56, 3629
4. Paterson, L.; Yeuna, K. S.: Ward, R. A., Cumming, J. G. J. Am Chem. Soc. 1994, 116, 9391.
5. Gunasekera, S. P.; Gunasekera, M.; Longley, R. E.: Schalte, G. K. J. Org. Chem. 1990, 55, 4912 (erratum: 1991, 56, 1346).
6. Nerenberg, J. B., Hung, D. T.: Somers, P. K.: Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 12621.
7. Fusetani, N.: Matsunaga, S.: Matsumoto, H.; Takebayashi, Y. J. Am. Chem. Soc. 1990, 112, 7053.
8. Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570.
9. Maryanoff, B. E.; Qiu, X. Y.; Padmanabhan, K. P.; Tulinsky, A. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8048.
10. Bewley, C. A.; Debitus, C.; Faulkner, D. J. J. Am. Chem. Soc. 1994, 116, 7631.
11. Bewley, C. A.: Faulkner, D. J. J. Org. Chem. 1994, 59, 4849.
12. 7 to prevent tautomerization between NH-1 and NH-3 of the inudazole ring.
13. (a) Piantim, U.; Sorenson, O. W.; Ernst, R. R. J. Am. Chem. Soc. 1982, 104, 6800.
14. (b) Rance, M: Sorenson. O W ; Bodenhausen, G., Wagner, G.; Ernst, R. R.; Wuthrich. K. Biochem. Biophys. Res. Comm. 1983, 117, 479.
15. Braunschweiler, L.: Ernst, R. R. J. Magn. Reson. 1983, 53, 521.
16. Summers, M. F.; Marzilli, L. G.: Bax, A. J. Am. Chem. Soc. 1986, 108, 4285.
17. (a) Bothner-By, A. A.: Stephens, R. L.: Lee, J., Warren, C. D.; Jeanloz, R. W. J. Am. Chem. Soc. 1984, 106, 811.
18. (b) Bax, A. and Davis. D. G. J. Magn. Reson. 1985, 63, 207.
19. Blaskovich, M. A.: Lajoie, G. A. J. Am. Chem. Soc. 1993, 115, 5021.
20. Schmidt, U.: Mundinser, K., Riedl, B., Haas, G.; Lau, R. Synthesis 1992, 1201.
21. Van Rheenan, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 1973.
22. Kolb, H. C.: Van Nieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483.
23. Nishi, M.; Isono, K.; Izaki, K. Agric. Biol. Chem. 1981, 45, 895.
24. Ubukata, M.: Uramoto, M.; Isono, K. Tetrahedron Lett. 1984, 25, 423.
25. Shimada, N.; Morimoto, K.; Naganawa, H.; Takita, T.: Hamada, M.; Maeda, K.; Takeuchi, T.; Umezawa, H. J. Antibiot. 1981, 34, 1613.
26. Komori, T.; Ezaki, M.; Kino, E.; Kohsaka, M.; Aoki, H.; Imanaka, H. J. Antibiol. 1985, 38, 691.
27. Tentative structures for aciculitamides A and B were proposed at the 7th International Symposium on Marine Natural Products (Capri, 1993), but by the time the proceedings were published we had gathered enough data to indicate that a portion of the proposed structure would have to be revised. The majority of the structural assignment remains unaltered. Faulkner, D. J.; He, H.; Unson, M. D.; Bewley, C. A.; Carson, M. J. Gazz. Chim. Ital. 1993, 123, 301.
28. Ryang, H.-S.; Foote, C. S. J. Am. Chem. Soc. 1979, 101, 6683.
29. Acar, J. F.; Goldstein, F. W. In Antibiotics in Laboratory Medicine, 2nd ed.; Lorian, V., Ed.; Williams & Wilkins: Baltimore, MD, 1986; Chapter 2.