Cytotoxic pyrroloiminoquinones from four new species of South African Latrunculid sponges

Journal of Natural Products

Volumn 67, Issue 8, 2004, Pages 1268-1276

  Antunes, Edith M ^a   Beukes, Denzil R ^a   Kelly, Michelle ^b   Samaai, Toufiek ^c   Barrows, Louis R ^d   Marshall, Kathryn M ^d   Sincich, Catherine ^e   Davies Coleman, Michael T ^a  

^a RHODES UNIVERSITY   (South Africa)

^b NATIONAL INSTITUTE OF WATER AND ATMOSPHERIC RESEARCH   (New Zealand)

^c UNIVERSITY OF KWAZULU NATAL   (South Africa)

^d UNIVERSITY OF UTAH   (United States)

^e UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINODISCORHABDIN D; 1 METHOXYDISCORHABDIN D; 14 BROMO 1 HYDROXYDISCORHABDIN V; 14 BROMO 3 DIHYDRO 7,8 DEHYDRODISCORHABDIN C; 3 DIHYDRO 7,8 DEHYDRODISCORHABDIN C; DISCORHABDIN H; DISCORHABDIN V; DNA TOPOISOMERASE; PYRROLOIMINOQUINONE; QUINONE DERIVATIVE; TSITSIKAMMAMINE; TSITSIKAMMAMINE A N 18 OXIME; TSITSIKAMMAMINE B N 18 OXIME; UNCLASSIFIED DRUG;

ACYLATION; ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CHEMICAL STRUCTURE; CHIRAL CHROMATOGRAPHY; CYTOTOXICITY; ENZYME INHIBITION; GAS CHROMATOGRAPHY; INTERCALATION COMPLEX; LATRUNCULIA; LATRUNCULIA BELLAE; MASS SPECTROMETRY; OZONOLYSIS; PROTEIN MOTIF; PROTON NUCLEAR MAGNETIC RESONANCE; SOUTH AFRICA; SPECTROSCOPY; SPONGE (PORIFERA); STEREOCHEMISTRY; STRONGYLODESMA ALGOAENSIS; STRUCTURE ANALYSIS; TSITSIKAMMA FAVUS; TSITSIKAMMA PEDUNCULATA;

ALKALOIDS; ANIMALS; ANTINEOPLASTIC AGENTS; DNA TOPOISOMERASES, TYPE I; DRUG SCREENING ASSAYS, ANTITUMOR; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HCT116 CELLS; HISTIDINE; HUMANS; MOLECULAR STRUCTURE; PORIFERA; SOUTH AFRICA;

LATRUNCULIA; LATRUNCULIDAE; PEDUNCULATA; PORIFERA;

EID: 4344707750     PISSN: 01633864     EISSN: None     Source Type: Journal    
DOI: 10.1021/np034084b     Document Type: Article

References (39)

1. Kelly, M.; Samaai, T. Family Latrunculiidae Topsent, 1922. In System Porifera: A Guide to the Classification of Sponges; Hooper, J. N. A., Van Soest, R. W. M., Eds.; Kluwer/Plenum Academic: New York, 2002; pp 718-729.
2. Samaai, T.; Gibbons, M. J.; Kelly, M.; Davies-Coleman, M. T. Zootaxa 2003, 371, 1-26.
3. Hooper, G. J.; Davies-Coleman, M. T.; Kelly-Borges, M.; Coetzee, P. S. Tetrahedron Lett. 1996, 37, 7135-7138.
4. Sakemi, S.; Sun, H. H.; Jefford, C. W.; Bernardinelli, G. Tetrahedron Lett. 1989, 30, 2517-2520.
5. Sun, H. H.; Sakemi, S.; Burres, N.; McCarthy, P. J. J. Org. Chem. 1990, 55, 4964-4966.
6. Gunasekera, S. P.; McCarthy, P. J.; Longley, R. E.; Pomponi, S. A.; Wright, A. E. J. Nat. Prod. 1999, 62, 1208-1211.
7. Gunasekera, S. P.; Zuleta, I. A.; Longley, R. E.; Wright, A. E.; Pomponi, S. A. J. Nat. Prod. 2003, 66, 1615-1617.
8. Stierle, D. B.; Faulkner, D. J. J. Nat. Prod. 1991, 54, 1134-1136.
9. Carney, J. R.; Scheuer, P. J.; Kelly-Borges, M. Tetrahedron 1993, 49, 8483-8486.
10. Perry, N. B.; Blunt, J. W.; McCombs, J. D.; Munro, M. H. G. J. Org. Chem. 1986, 51, 5476-5478.
11. Perry, N. B.; Blunt, J. W.; Munro, H. M. G. Tetrahedron 1988, 44, 1727-1734.
12. Perry, N. B.; Blunt, J. W.; Higa, T.; Sakai, R.; Munro, M. H. G. J. Org. Chem. 1988, 53, 4127-4128.
13. Yang, A.; Baker, B. J.; Grimwade, J.; Leonard, A.; McClintock, J. B. J. Nat. Prod. 1995, 58, 1596-1599.
14. Dijoux, M. G.; Gamble, W. R.; Hallock, Y. F.; Cardellina, J. H.; Van Soest, R.; Boyd, M. R. J. Nat. Prod. 1999, 62, 636-637.
15. Ford, J.; Capon, R. J. Nat. Prod. 2000, 63, 1527-1528.
16. Kobayashi, J.; Cheng, J.-F.; Ishibashi, N.; Nakamura, H.; Ohizumi, Y.; Hirata, Y.; Sasaki, T.; Lu, H.; Clardy, J. Tetrahedron Lett. 1987, 28, 4939-4942.
17. Cheng, J.; Ohizumi, Y.; Wälchli, M. R.; Nakamura, H.; Hirata, Y.; Sasaki, T.; Kobayashi, J. J. Org. Chem. 1988, 53, 4127-4128.
18. Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.; Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1993, 115, 1632-1638.
19. Schmidt, E. W.; Harper, M. K.; Faulkner, D. J. J. Nat. Prod. 1995, 58, 1861-1867.
20. Venables, D. A.; Barrows, L. R.; Lassota, P.; Ireland, C. M. Tetrahedron Lett. 1997, 30, 2517-2520.
21. Venables, D. A.; Concepción, G. P.; Matsumoto, S. S.; Barrows, L. R.; Ireland, C. M. J. Nat. Prod. 1997, 60, 408-410.
22. Chang, L. C.; Otero-Quintero, S.; Hooper, J. N. A.; Bewley, C. A. J. Nat. Prod. 2002, 65, 776-778.
23. Fu, X.; Ng, P.; Schmitz, F. J.; Hossain, M. B.; van der Helm, D.; Kelly-Borges, M. J. Nat. Prod. 1996, 59, 1104-1106.
24. Urban, S.; Hickford, S. J. H.; Blunt, J. W.; Munro, M. H. G. Curr. Org. Chem. 2000, 4, 765-807.
25. Beukes, D. R.; Davies-Coleman; M. T.; Kelly-Borges, M.; Harper, M. K.; Faulkner, D. J. J. Nat. Prod. 1998, 61, 699-701. McPhail, K. L.; Rivett, D. E. A.; Lack, D. E.; Davies-Coleman, M. T. Tetrahedron 2000, 56, 9391-9396.
26. Beukes, D. R.; Davies-Coleman; M. T.; Kelly-Borges, M.; Harper, M. K.; Faulkner, D. J. J. Nat. Prod. 1998, 61, 699-701. McPhail, K. L.; Rivett, D. E. A.; Lack, D. E.; Davies-Coleman, M. T. Tetrahedron 2000, 56, 9391-9396.
27. Copp, B. R.; Fulton, K. F.; Perry, N. B.; Blunt, J. W.; Munro, M. H. G. J. Org. Chem. 1994, 59, 8233-8238.
28. Blunt, J. W.; Munro, M. H. G.; Battershill, C. N.; Copp, B. R.; McCombs, J. D.; Perry, N. B.; Prinsep, M.; Thompson, A. M. New J. Chem. 1990, 14, 761-775.
29. Crewes, P.; Rodriguez, J.; Jaspars, M. Organic Structure Analysis; Oxford University Press: New York, 1998; p 141.
30. Matsunuga, S.; Shinoda, Katsumi; Fusetani, N. Tetrahedron Lett. 1993, 34, 5953-5954.
31. Ishibashi, M.; Tsuda, M.; Ohizumi, Y.; Sasaki, T.; Kobayashi, J. Experentia 1991, 47, 299-300.
32. Copp, B. R.; Ireland, C. M.; Barrows, L. R. J. Org. Chem. 1991, 56, 4596-4597.
33. Lill, R. E.; Major, D. A.; Blunt, J. W.; Munro, M. H. G.; Battershill, C. N.; McLean, M. G.; Baxter, R. L. J. Nat. Prod. 1995, 58, 306-311.
34. The spectral data for discorhabdins E-M were presented at the New Zealand Institute of Chemistry Conference (Dec 7-10, 1993) and later at the 37th Annual Meeting of the American Society of Pharmacognosy, 1996.
35. Beukes, D. R. PhD Thesis, Rhodes University, 2000.
36. 13C data for this compound in the mainstream chemical literature necessitated the inclusion of these data in the Experimental Section.
37. Kokoshka, J. M.; Capson, T. L.; Holden, J. A.; Ireland, C. M.; Barrows, L. R. Anti-Cancer Drugs 1996, 7, 758-765.
38. Matsumoto, S. S.; Haughey, H. M.; Schmehl, D. M.; Venables, D. A.; Ireland, C. M.; Holden, J. A.; Barrows, L. R. Anticancer Drugs 1999, 10, 39-45.
39. Barrows, L. R.; Radisky, D. C.; Copp, B. R.; Swaffar, D. S.; Kramer, R. A.; Warters, R. L.; Ireland, C. M. Anti-Cancer Drug Des. 1993, 8, 333-347.