Motualevic acids A-F, antimicrobial acids from the sponge Siliquariaspongia sp.

Organic Letters

Volumn 11, Issue 5, 2009, Pages 1087-1090

  Keffer, Jessica L ^a   Plaza, Alberto ^a   Bewley, Carole A ^a  

^a NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTAZIRINE; ANTIINFECTIVE AGENT; AZIRINE DERIVATIVE; BROMINATED HYDROCARBON;

ANIMAL; ARTICLE; BIOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; ISOLATION AND PURIFICATION; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIOLOGICAL EXAMINATION; PENICILLIN RESISTANCE; SPONGE (PORIFERA); STAPHYLOCOCCUS AUREUS; SYNTHESIS;

ANIMALS; ANTI-BACTERIAL AGENTS; AZIRINES; HYDROCARBONS, BROMINATED; MARINE BIOLOGY; METHICILLIN RESISTANCE; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PORIFERA; STAPHYLOCOCCUS AUREUS;

EID: 64349100196     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol802890b     Document Type: Article

References (25)

1. Levy, S. B.; Marshall, B. Nat. Med. 2004, 10, S122-S129.
2. Payne, D. J.; Gwynn, M. N.; Holmes, D. J.; Pompliano, D. L. Nat. Rev. Drug Discov. 2007, 6, 29-40.
3. Walsh, C. T. Nat. ReV. Microbiol. 2003, 1, 65-70.
4. Newman, D. J.; Cragg, G. M. J. Nat. Prol. 2007, 70, 461-477.
5. Plaza, A.; Gustchina, E.; Baker, H. L.; Kelly, M.; Bewley, C. A. J. Nat. Prod. 2007, 70, 1753-1760.
6. Plaza, A.; Bifulco, G.; Keffer, J. L.; Lloyd, J. R.; Baker, H. L.; Bewley, C. A. J. Org. Chem. 2009, 74, 504-512.
7. (a) Bewley, C. A.; Faulkner, D. J. Angew. Chem., Int. Ed. 1998, 37, 2162-2178.
8. (b) Matsunaga, S.; Fusetani, N. Curr. Org. Chem. 2003, 7, 945.
9. (c) Piel, J.; Hui, D.; Wen, G.; Butzke, D.; Platzer, M.; Fusetani, N.; Matsunaga, S. Proc. Natl. Acad. Sci. U. S. A. 2004, 101, 16222-16227.
10. Extract obtained from the NCI Open Repository.
11. Salomon, C. E.; Williams, D. H.; Faulkner, D. J. J. Nat. Prod. 1995, 58, 1463-1466.
12. Skepper, C. K.; Molinski, T. F. J. Org. Chem. 2007, 73, 2592-2597.
13. Molinski, T. F.; Ireland, C. M. J. Org. Chem. 1988, 53, 2103-2105.
14. Davis, F. A.; Reddy, G. V.; Liu, H. J. Am. Chem. Soc. 1995, 117, 3651-3652.
15. YMC chiral NEA column, 0.01% TFA in 70:30 hexanes/i-PrOH.
16. Because compounds containing free acids exhibited the strongest antimicrobial activity in disk diffusion assays, assays were performed in liquid cultures to assure diffusion was not charge dependent.
17. (a) Stapley, E. O.; Hendlin, D.; Jackson, M.; Miller, A. K.; Hernandez, S.; Mata, J. M. J. Antibiot. 1971, 24, 42-47.
18. (b) Miller, T. W.; Tristram, E. W.; Wolf, F. J. J. Antibiot. 1971, 24, 48-50.
19. Lowden, P. A. S. Aziridine Natural Products - Discovery, Biological Acitivity and Biosynthesis. In Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinham 2006; pp 399-442.
20. Vaillincourt, F. H.; Yeh, E.; Vosburg, D. A.; O'Connor, S. E.; Walsh, C. T. Nature 2005, 436, 1191-1194.
21. (a) Hirsh, S.; Carmely, S.; Kashman, Y. Tetrahedron 1987, 43, 3257-3261.
22. (b) Morinaka, B. I.; Skepper, C. K.; Molinski, T. F. Org. Lett. 2007, 9, 1975-1978.
23. (c) Brantley, S. E.; Molinski, T. F.; Preston, C. M.; DeLong, E. F. Tetrahedron 1995, 51, 7667-7672.
24. (d) Li, Y.; Ishibashi, M.; Sasaki, T.; Kobayashi, J. J. Chem. Res., Synop. 1995, 126-127.
25. (e) Taniguchi, M.; Uchio, Y.; Yasumoto, K.; Kusumi, T.; Ooi, T. Chem. Pharm. Bull. 2008, 56, 378-382.