Cytotoxic halogenated macrolides and modified peptides from the apratoxin-producing marine cyanobacterium Lyngbya bouillonii from Guam

Journal of Natural Products

Volumn 73, Issue 9, 2010, Pages 1544-1552

  Matthew, Susan ^a   Salvador, Lilibeth A ^a   Schupp, Peter J ^b   Paul, Valerie J ^c   Luesch, Hendrik ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b UNIVERSITY OF GUAM MARINE LABORATORY   (Guam)

^c SMITHSONIAN MARINE STATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 EPI LYNGBYALOSIDE; 27 DEOXYLYNGBYABELLIN A; APRATOXIN A; APRATOXIN C; LAINGOLIDE B; LYNGBYABELLIN A; LYNGBYABELLIN B; LYNGBYABELLIN J; LYNGBYALOSIDE; LYNGBYALOSIDE C; LYNGBYAPEPTIN D; MACROLIDE; NATURAL PRODUCT; PEPTIDE; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; DEPSIPEPTIDE; HALOGENATED HYDROCARBON; LYNGBYATOXIN;

ARTICLE; BROMINATION; CANCER CELL CULTURE; CARCINOMA CELL; CHLORINATION; COLORECTAL CARCINOMA; CYTOSKELETON; CYTOTOXICITY; EXTRACT; FAMILY; GUAM; HALOGENATION; HELA CELL; HUMAN; HUMAN CELL; IC 50; ISOMERISM; LYNGBYA BOUILLONII; MARINE BACTERIUM; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE ANALYSIS; UTERINE CERVIX CARCINOMA; CHEMICAL STRUCTURE; CHEMISTRY; CYANOBACTERIUM; DRUG SCREENING; HELA CELL LINE; HT 29 CELL LINE; ISOLATION AND PURIFICATION; MARINE BIOLOGY; STEREOISOMERISM;

LYNGBYA BOUILLONII;

ANTINEOPLASTIC AGENTS; CYANOBACTERIA; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; GUAM; HELA CELLS; HT29 CELLS; HUMANS; HYDROCARBONS, HALOGENATED; LYNGBYA TOXINS; MACROLIDES; MARINE BIOLOGY; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STEREOISOMERISM;

EID: 77957242141     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np1004032     Document Type: Article

References (35)

1. Tan, L. T. Phytochemistry 2007, 68, 954-979
2. Hoffmann, L. and Demoulin, V. Belg. J. Bot. 1991, 124, 82-88
3. Luesch, H. The search for new anticancer drugs from marine cyanobacteria and investigations on the biosynthesis of cyanobacterial metabolites. Ph.D. Thesis, University of Hawaii, Manoa, HI, 2002.
4. Luesch, H., Yoshida, W. Y., Moore, R. E., Paul, V. J., and Corbett, T. H. J. Am. Chem. Soc. 2001, 123, 5418-5423
5. Luesch, H., Yoshida, W. Y., Moore, R. E., Paul, V. J., and Mooberry, S. L. J. Nat. Prod. 2000, 63, 611-615
6. Luesch, H., Yoshida, W. Y., Moore, R. E., and Paul, V. J. J. Nat. Prod. 2000, 63, 1437-1439
7. Luesch, H., Yoshida, W. Y., Moore, R. E., and Paul, V. J. J. Nat. Prod. 1999, 62, 1702-1706
8. Matthew, S., Schupp, P. J., and Luesch, H. J. Nat. Prod. 2008, 71, 1113-1116
9. Luesch, H., Yoshida, W. Y., Moore, R. E., and Paul, V. J. Bioorg. Med. Chem. 2002, 10, 1973-1978
10. Luesch, H., Yoshida, W. Y., Moore, R. E., and Paul, V. J. J. Nat. Prod. 2000, 63, 1106-1112
11. Banner, D. M. and Banner, A. H. Rec. Aust. Mus. Suppl. 1982, 34, 359-362
12. Cruz-Rivera, E. and; Paul, V. J. Proceedings of 9th International Coral Reef Symposium, Bali, Indonesia, October 23-27, 2000; International Society for Reef Studies: Melbourne, Florida.
13. Cruz-Rivera, E. and Paul, V. J. Coral Reefs 2006, 25, 617-627
14. Brey, W., Edison, A. S., Nast, R. E., Rocca, J. R., Saha, S., and Withers, R. S. J. Magn. Reson. 2006, 179, 290-293
15. Liu, Y., Law, B. K., and Luesch, H. Mol. Pharmacol. 2009, 76, 91-104
16. Klein, D., Braekman, J. C., Daloze, D., Hoffmann, L., and Demoulin, V. J. Nat. Prod. 1997, 60, 1057-1059
17. Tan, L. T., Márquez, B. L., and Gerwick, W. H. J. Nat. Prod. 2002, 65, 925-928
18. Luesch, H., Yoshida, W. Y., Harrigan, G. G., Doom, J. P., Moore, R. E., and Paul, V. J. J. Nat. Prod. 2002, 65, 1945-1948
19. Milligan, K. E., Marquez, B. L., Williamson, R. T., and Gerwick, W. H. J. Nat. Prod. 2000, 63, 1440-1443
20. Klein, D., Braekman, J. C., Daloze, D., Hoffmann, L., and Demoulin, V. Tetrahedron Lett. 1996, 37, 7519-7520
21. Klein, D., Braekman, J. C., Daloze, D., Hoffmann, L., Castillo, G., and Demoulin, V. J. Nat. Prod. 1999, 62, 934-936
22. Klein, D., Braekman, J. C., Daloze, D., Hoffmann, L., Castillo, G., and Demoulin, V. Tetrahedron Lett. 1999, 40, 695-696
23. Sone, H., Kigoshi, H., and Yamada, K. J. Org. Chem. 1996, 61, 8956-8960
24. Luesch, H., Yoshida, W. Y., Moore, R. E., and Paul, V. J. Tetrahedron 2002, 58, 7959-7966
25. Williams, P. G., Luesch, H., Yoshida, W. Y., Moore, R. E., and Paul, V. J. J. Nat. Prod. 2003, 66, 595-598
26. Han, B., McPhail, K. L., Gross, H., Goeger, D. E., Mooberry, S. L., and Gerwick, W. H. Tetrahedron 2005, 61, 11723-11729
27. Yokokawa, F., Sameshima, H., Katagiri, D., Aoyama, T., and Shioiri, T. Tetrahedron 2002, 58, 9445-9458
28. Pang, H., Xu, Z., Chen, Z., and Ye, T. Lett. Org. Chem. 2005, 2, 699-702
29. Marquez, B. L., Watts, K. S., Yokochi, A., Roberts, M. A., Verdier-Pinard, P., Jimenez, J. I., Hamel, E., Scheuer, P. J., and Gerwick, W. H. J. Nat. Prod. 2002, 65, 866-871
30. Preciado, A. and Williams, P. G. J. Org. Chem. 2008, 73, 9228-9234
31. Cardellina, J. H., Marner, F.-J., and Moore, R. E. J. Am. Chem. Soc. 1979, 101, 240-242
32. Milligan, K. E., Márquez, B., Williamson, R. T., Davies-Coleman, M., and Gerwick, W. H. J. Nat. Prod. 2000, 63, 965-968
33. Appleton, D. R., Sewell, M. A., Berrid, M. V., and Copp, B. R. J. Nat. Prod. 2002, 65, 630-631
34. Nogle, L. M. and Gerwick, W. H. J. Nat. Prod. 2003, 66, 217-220
35. Kwan, J. C., Teplitski, M., Gunasekera, S. P., Paul, V. J., and Luesch, H. J. Nat. Prod. 2010, 73, 463-466