Hurghadolide A and swinholide I, potent actin-microfilament disrupters from the red sea sponge Theonella swinhoei

Journal of Natural Products

Volumn 69, Issue 1, 2006, Pages 154-157

  Youssef, Diaa T A ^a   Mooberry, Susan L ^b  

^a Suez Canal University   (Egypt)

^b SOUTHWEST FOUNDATION FOR BIOMEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIN; ANTINEOPLASTIC AGENT; HURGHADOLIDE A; LACTONE; MACROLIDE; SWINHOLIDE A; SWINHOLIDE I; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CELL STRAIN HCT116; COLON ADENOCARCINOMA; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CYTOSKELETON; DRUG CYTOTOXICITY; DRUG ISOLATION; HUMAN; HUMAN CELL; HYDROXYLATION; IC 50; IN VITRO STUDY; MASS SPECTROMETRY; MICROFILAMENT; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SEA; SPONGE (PORIFERA); STRUCTURE ANALYSIS; THEONELLA; THEONELLA SWINHOEI;

ACTINS; ANIMALS; ANTINEOPLASTIC AGENTS; CYTOSKELETON; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INDIAN OCEAN; MACROLIDES; MICROFILAMENTS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PORIFERA; TUMOR CELLS, CULTURED;

CANDIDA ALBICANS; PORIFERA; THEONELLA; THEONELLA SWINHOEI;

EID: 32644452774     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np050404a     Document Type: Article

References (29)

1. Blunt, J. W.; Copp, B. R.; Munro, M. H. G.; Northcote, P. T.; Prinsep, M. R. Nat. Prod. Rep. 2005, 22, 15-61, and the previous reviews in this series.
2. Kashman, Y.; Carmely, S. Tetrahedron Lett. 1985, 26, 511-514.
3. Kobayashi, M.; Tanaka, J.; Katori, T.; Matsuura, M.; Kitagawa, I. Tetrahedron Lett. 1989, 22, 2963-2966.
4. (a) Kobayashi, M.; Tanaka, J.; Katori, T.; Matsuura, M.; Yamashita, M.; Kitagawa, I. Chem. Pharm. Bull. 1990, 38, 2409-2418.
5. (b) Kitagawa, I.; Kobayashi, M.; Katori, T.; Yamashita, M.; Tanaka, J.; Doi, M.; Ishida, T. J. Am. Chem. Soc. 1990, 112, 3710-3712.
6. (c) Doi, M.; Ishida, T.; Kobayashi, M.; Kitagawa, I. J. Org. Chem. 1991, 56, 3629-3632.
7. (a) Kobayashi, M.; Tanaka, J.; Katori, T.; Kitagawa, I. Chem. Pharm. Bull. 1990, 38, 2960-2966.
8. (b) Tsukamoto, S.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Chem. Soc., Perkin Trans, 1 1991, 3185-3188.
9. (c) Dumdei, E. J.; Blunt, J. W.; Munro, M. H. G.; Pannell, L. K. J. Org. Chem. 1997, 62, 2635-2639.
10. (d) Sakai, R.; Higa, T.; Kashman, Y. Chem. Lett. 1986, 1499-1502.
11. (e) Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K.; Sakai, R.; Higa, T.; Kashman, Y. Tetrahedron Lett. 1987, 28, 6225-6228.
12. (f) Tanaka, J.; Higa, T.; Motomasa, K.; Kitagawa, I. Chem. Pharm. Bull. 1990, 38, 2967-2970.
13. (g) Todd, J. S.; Alvi, K. A.; Crews, P. Tetrahedron Lett. 1992, 33,441-442.
14. (a) Bewley, C. A.; Holland, N. D.; Faulkner, D. J. Experientia 1996, 52, 716-722.
15. (b) Andrianasolo, E. H.; Gross, H.; Goeger, D.; Musafija-Girt, M.; McPhail, K.; Leal, R. M.; Mooberry, S. L.; Gerwick, W. H. Org. Lett. 2005, 7, 1375-1378.
16. (a) Youssef, D. T. A.; Shaala, L. A.; Emara, S. J. Nat. Prod. 2005, 68, 1782-1784.
17. (b) Youssef, D. T. A. J. Nat. Prod. 2005, 68, 1416-1419.
18. (c) Youssef, D. T. A. J. Nat. Prod. 2004, 67, 112-114.
19. (d) Youssef, D. T. A.; van Soest, R. W. M.; Fusetani, N. J. Nat. Prod. 2003, 66, 861-862.
20. (e) Youssef, D. T. A.; van Soest, R. W. M.; Fusetani, N. J. Nat. Prod. 2003, 66, 679-681.
21. (f) Youssef, D. T. A.; Yamaki, R. K.; Kelly, M.; Scheuer, P. J. J. Nat. Prod. 2002, 65, 2-6.
22. (g) Youssef, D. T. A.; Yoshida, W. Y.; Kelly, M.; Scheuer, P. J. J. Nat. Prod. 2001, 64, 1332-1335.
23. (h) Youssef, D. T. A.; Yoshida, W. Y.; Kelly, M.; Scheuer, P. J. J. Nat. Prod. 2000, 63, 1406-1410.
24. The numbering 1′, 2′, 3′, 4′, and 5′ in hurghadolide A (3) corresponds to 1′, 4′, 5′, 6′, and 7′ in swinholide A (1), respectively.
25. Harrigan, G. G.; Yoshida, W.; Moore, R. E.; Nagle, D. G.; Park, P. U.; Biggs, J.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H.; Valeriote, F. A. J. Nat. Prod. 1998, 61, 1221-1225.
26. Bubb, M. R.; Spector, I.; Bershadsky, A. D.; Korn, E. D. J. Biol. Chem. 1995, 270, 3463-3466.
27. Saito, S.; Watabe, S.; Ozaki, H.; Kobayashi, M.; Suzuki, T.; Kobayashi, H.; Fusetani, N.; Karaki, H. J. Biochem. 1998, 123, 571-578.
28. Terry, D. R.; Spector, I.; Higa, T.; Bubb, M. R. J. Biol. Chem. 1997, 272, 7841-7845.
29. Soria-Mercado, I. E.; Prieto-Davo, A.; Jensen, P. R.; Fenical, W. J. Nat. Prod. 2005, 68, 904-910.