Elaiomycins D-F, antimicrobial and cytotoxic azoxides from streptomyces sp. strain HKI0708

Journal of Natural Products

Volumn 75, Issue 10, 2012, Pages 1729-1734

  Ding, Ling ^a   Ndejouong, Basile Le Sage Tchize ^a   Maier, Armin ^b   Fiebig, Heinz Herbert ^b   Hertweck, Christian ^a,c  

^a HANS KNÖLL INSTITUTE   (Germany)

^b CHARLES RIVER LABORATORIES   (United States)

^c FRIEDRICH SCHILLER UNIVERSITY JENA   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AZOXY DERIVATIVE; ELAIOMYCIN D; ELAIOMYCIN E; ELAIOMYCIN F; NATURAL PRODUCT; POLYPEPTIDE ANTIBIOTIC AGENT; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIUM ISOLATION; BIOSYNTHESIS; CANCER CELL; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYTOTOXICITY; HETERONUCLEAR MULTIPLE BOND CORRELATION; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STREPTOMYCES; STRUCTURE ACTIVITY RELATION; UMBILICAL VEIN ENDOTHELIAL CELL;

ANTI-BACTERIAL AGENTS; ANTI-INFECTIVE AGENTS; ASPERGILLUS; AZO COMPOUNDS; HUMANS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM; STEREOISOMERISM; STREPTOMYCES; STRUCTURE-ACTIVITY RELATIONSHIP;

ASPERGILLUS; STREPTOMYCES SP.;

EID: 84868025192     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np300329m     Document Type: Article

References (28)

1. Patai, S.; Boyd, G. V. The Chemistry of the Hydrazo, Azo and Azoxy Groups, Vol. 2; Synthesis and Reactions of Hydrazo, Azo and Azoxy Compounds; John Wiley & Sons: New York, 1997; DOI: 10.1002/0470023503.ch10.
2. Schoental, R. Nature 1969, 221, 765-766
3. Castillo-Guevara, C.; Rico-Gray, V. J. Torrey. Bot. Soc. 2003, 130, 206-217
4. Claydon, N. J. Invertebr. Pathol. 1978, 32, 319-324
5. Fujiu, M.; Sawairi, S.; Shimada, H.; Takaya, H.; Aoki, Y.; Okuda, T.; Yokose, K. J. Antibiot. 1994, 47, 833-835
6. Yamato, M.; Iinuma, H.; Naganawa, H.; Yamagishi, Y.; Hamada, M.; Masuda, T.; Umezawa, H.; Abe, V.; Hori, M. J. Antibiot. 1986, 39, 184-191
7. Garg, R. P.; Qian, X. L.; Alemany, L. B.; Moran, S.; Parry, R. J. Proc. Natl. Acad. Sci. 2008, 105, 6543-6547
8. Garg, R. P.; Alemany, L. B.; Moran, S.; Parry, R. J. J. Am. Chem. Soc. 2009, 131, 9608-9609
9. Haskell, T. H.; Ryder, A.; Bartz, Q. R. Antibiot. Chemother. 1954, 4, 141-144
10. Winkler, R.; Hertweck, C. Angew. Chem., Int. Ed. 2005, 44, 4083-4087
11. Parry, R. J.; Rao, H. S. P.; Mueller, J. J. Am. Chem. Soc. 1982, 104, 339-340
12. Parry, R. J.; Mueller, J. V. J. Am. Chem. Soc. 1984, 106, 5764-5765
13. He, J.; Roemer, E.; Lange, C.; Huang, X.; Maier, A.; Kelter, G.; Jiang, Y.; Xu, L. H.; Menzel, K. D.; Grabley, S.; Fiebig, H. H.; Jiang, C. L.; Sattler, I. J. Med. Chem. 2007, 50, 5168-5175
14. Tchize Ndejouong, B. L. S.; Sattler, I.; Maier, A.; Kelter, G.; Menzel, K. D.; Fiebig, H. H.; Hertweck, C. J. Antibiot. 2010, 63, 359-363
15. Ueberschaar, N.; Ndejouong, B. L. S. T.; Ding, L.; Maier, A.; Fiebig, H. H.; Hertweck, C. Bioorg. Med. Chem. Lett. 2011, 21, 5839-5841
16. Helaly, S. E.; Pesic, A.; Fiedler, H. P.; Süssmuth, R. D. Org. Lett. 2011, 13, 1052-1055
17. McGahren, W. J.; Kunstmann, M. P. J. Am. Chem. Soc. 1970, 92, 1587-90
18. McGahren, W. J.; Kunstmann, M. P. J. Org. Chem. 1972, 37, 902-906
19. Taylor, K. G.; Ramdas, S. I.; Swigert, J. L. J. Org. Chem. 1976, 41, 1146-1152
20. Prado, A.; Ledezma, J.; Cubilla-Rios, L.; Bede, J. C.; Windsor, D. M. J. Chem. Ecol. 2011, 37, 736-740
21. Taylor, K. G.; Riehl, T. J. Am. Chem. Soc. 1972, 94, 250-255
22. Takahashi, Y.; Nakayama, M.; Watanabe, I.; Deushi, T.; Ishiwata, H.; Shiratsuchi, M.; Otani, G. J. Antibiot. 1989, 42, 1541-1546
23. Nakayama, M.; Takahashi, Y.; Itoh, H.; Kamiya, K.; Shiratsuchi, M.; Otani, G. J. Antibiot. 1989, 42, 1535-1540
24. Karlson, A. G. Antibiot. Chemother. 1962, 12, 446-449
25. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically, Approved Standard. NCCLS Document M7-A4, 4 th ed.; National Committee for Clinical Laboratory Standards: Villanova, PA, 1997.
26. Clinical and Laboratory Standards Institute. Reference method for broth dilution antifungal susceptibility testing of filamentous fungi; Approved standard, 2 nd ed., CLSI document M38-A2; Clinical and Laboratory Standards Institute: Wayne, PA, 2008.
27. Scherlach, K.; Partida-Martinez, L. P.; Dahse, H. M.; Hertweck, C. J. Am. Chem. Soc. 2006, 128, 11529-11536
28. Dengler, W. A.; Schulte, J.; Berger, D. P.; Mertelsmann, R.; Fiebig, H. H. Anti-Cancer Drugs 1995, 6, 522-532