Veraguamides A-G, cyclic hexadepsipeptides from a dolastatin 16-producing cyanobacterium Symploca cf. hydnoides from Guam

Journal of Natural Products

Volumn 74, Issue 5, 2011, Pages 917-927

  Salvador, Lilibeth A ^a   Biggs, Jason S ^b   Paul, Valerie J ^c   Luesch, Hendrik ^a  

^a UNIVERSITY OF FLORIDA   (United States)

^b UNIVERSITY OF GUAM   (Guam)

^c SMITHSONIAN MARINE STATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; CYTOTOXIC AGENT; DOLASTATIN 16; HYDROXYACID; PACLITAXEL; PHENYLGLYCINE; TETRAHYDROVERAGUAMIDE A; UNCLASSIFIED DRUG; VERAGUAMIDE A; VERAGUAMIDE B; VERAGUAMIDE C; VERAGUAMIDE D; VERAGUAMIDE E; VERAGUAMIDE F; VERAGUAMIDE G;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL VIABILITY; COLORECTAL CARCINOMA; CONTROLLED STUDY; CYANOBACTERIUM; CYTOTOXICITY; DRUG DEGRADATION; DRUG STRUCTURE; FEMALE; GUAM; HELA CELL; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SYMPLOCA HYDNOIDES;

ANTINEOPLASTIC AGENTS; CYANOBACTERIA; DEPSIPEPTIDES; DRUG SCREENING ASSAYS, ANTITUMOR; FEMALE; GUAM; HELA CELLS; HT29 CELLS; HUMANS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP;

SYMPLOCA HYDNOIDES;

EID: 79957810219     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np200076t     Document Type: Article

References (28)

1. Tan, L. T. J. Appl. Phycol. 2010, 22, 659-676.
2. Nunnery, J. K.; Mevers, E.; Gerwick, W. H. Curr. Opin. Biotechnol. 2010, 21, 787-793.
3. Harrigan, G. G.; Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Nagle, D. G.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H.; Valeriote, F. A. J. Nat. Prod. 1998, 61, 1075-1077.
4. Luesch, H.; Moore, R. E.; Paul, V. J.; Mooberry, S. L.; Corbett, T. H. J. Nat. Prod. 2001, 64, 907-910.
5. Mooberry, S. L.; Leal, R. M.; Tinley, T. L.; Luesch, H.; Moore, R. E.; Corbett, T. H. Int. J. Cancer 2003, 104, 512-521.
6. Taori, K.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 1806-1807.
7. Liu, Y.; Salvador, L. A.; Byeon, S.; Ying, Y.; Kwan, J. C.; Law, B. K.; Hong, J.; Luesch, H. J. Pharmacol. Exp. Ther. 2010, 335, 351-361.
8. Pettit, G. R.; Xu, J.; Hogan, F.; Williams, M. D.; Doubek, D. L.; Schmidt, J. M.; Cerny, R. L.; Boyd, M. R. J. Nat. Prod. 1997, 60, 752-754.
9. The trivial names were assigned to conform with the naming by W. Gerwick and co-workers, who concurrently isolated members of this compound class: Mevers, E.; Liu, W. T.; Engene, N.; Mohimani, H.; Byrum, T.; Pevzner, P. A.; Dorrestein, P. C.; Gerwick, W. H. J. Nat. Prod. 2011, doi 10.1021.np200077f.
10. Edwards, D. J.; Marquez, B. L.; Nogle, L. M.; McPhail, K.; Goeger, D. E.; Roberts, M. A.; Gerwick, W. H. Chem. Biol. 2004, 11, 817-833.
11. Sone, H.; Kondo, T.; Kiryu, M.; Ishiwata, H.; Ojika, M.; Yamada, K. J. Org. Chem. 1995, 60, 4774-4781.
12. Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309-2315.
13. Tripathi, A.; Puddick, J.; Prinsep, M. R.; Lee, P. P.; Tan, L. T. Phytochemistry 2010, 71, 307-311.
14. Tripathi, A.; Puddick, J.; Prinsep, M. R.; Lee, P. P.; Tan, L. T. J. Nat. Prod. 2009, 72, 29-32.
15. Nogle, L. M.; Gerwick, W. H. J. Nat. Prod. 2002, 65, 21-24.
16. Bunyajetpong, S.; Yoshida, W. Y.; Sitachitta, N.; Kaya, K. J. Nat. Prod. 2006, 69, 1539-1542.
17. Tan, L. T.; Goh, B. P.; Tripathi, A.; Lim, M. G.; Dickinson, G. H.; Lee, S. S.; Teo, S. L. Biofouling 2010, 26, 685-695.
18. Montaser, R.; Abboud, K. A.; Paul, V. J.; Luesch, H. J. Nat. Prod. 2011, 74, 109-112.
19. Kimura, J.; Takada, Y.; Inayoshi, T.; Nakao, Y.; Goetz, G.; Yoshida, W. Y.; Scheuer, P. J. J. Org. Chem. 2002, 67, 1760-1767.
20. Harrigan, G. G.; Yoshida, W. Y.; Moore, R. E.; Nagle, D. G.; Park, P. U.; Biggs, J.; Paul, V. J.; Moobery, S. L.; Corbett, T. H.; Valeriote, F. A. J. Nat. Prod. 1998, 61, 1221-1225.
21. Williams, P. G.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2003, 66, 1356-1363.
22. Williams, D. E.; Burgoyne, D. L.; Rettig, S. J.; Andersen, R. J. J. Nat. Prod. 1993, 56, 545-551.
23. Luesch, H.; Williams, P. G.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J. J. Nat. Prod. 2002, 65, 996-1000.
24. We recorded the retention of the L-FDLA- and D-FDLA-derivatized Dml and its C-2 epimer (obtained by treatment with base) to obtain four different retention times.
25. Yabuuchi, T.; Kusumi, T. J. Org. Chem. 2000, 65, 397-404.
26. Davies-Coleman, M. T.; Dzeha, T. M.; Gray, C. A.; Hess, S.; Pannell, L. K.; Hendricks, D. T.; Arendse, C. E. J. Nat. Prod. 2003, 66, 712-715.
27. Harada, K.-I.; Fujii, K.; Mayumi, T.; Hibino, Y.; Suzuki, M.; Ikai, Y.; Oka, H. Tetrahedron Lett. 1995, 36, 1515-1518.
28. Fujii, K.; Ika, Y.; Oka, H.; Suzuki, M.; Harada, K. Anal. Chem. 1997, 69, 5146-5151.