Nannozinones and sorazinones, unprecedented pyrazinones from myxobacteria

Journal of Natural Products

Volumn 77, Issue 11, 2014, Pages 2545-2552

  Jansen, Rolf ^a   Sood, Sakshi ^a   Mohr, Kathrin I ^a   Kunze, Brigitte ^a   Irschik, Herbert ^a   Stadler, Marc ^a   Müller, Rolf ^a,b  

^a HELMHOLTZ CENTRE FOR INFECTION RESEARCH   (Germany)

^b SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; METHYL INDOLE 3 CARBOYXLATE; NANNOCHELIN A IRON COMPLEX; NANNOZINONE A; NANNOZINONE B; PIPERAZINEDIONE; PYRAZINE DERIVATIVE; PYRROLINE DERIVATIVE; SORAZINONE A; SORAZINONE B; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT; INDOLE DERIVATIVE; PYRROLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIUM ISOLATION; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DEUTERON NUCLEAR MAGNETIC RESONANCE; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; IC50; METABOLITE; MYXOCOCCALES; NANNOCYSTIS PUSILLA; NITROGEN NUCLEAR MAGNETIC RESONANCE; NOCARDIA; NONHUMAN; SORANGIUM CELLULOSUM; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; GRAM POSITIVE BACTERIUM; HUMAN; ISOLATION AND PURIFICATION; MICROBIAL SENSITIVITY TEST; MICROBIOLOGY; SPAIN;

MYXOCOCCALES;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; GRAM-POSITIVE BACTERIA; HUMANS; INDOLES; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYXOCOCCALES; PYRAZINES; PYRROLES; SOIL MICROBIOLOGY; SPAIN;

EID: 84913528467     PISSN: 01633864     EISSN: 15206025     Source Type: Journal    
DOI: 10.1021/np500632c     Document Type: Article

References (42)

1. Wenzel, S. C.; Müller, R. Curr. Opin. Drug Discovery Dev. 2009, 12, 220-230
2. Müller, R.; Wink, J. Int. J. Med. Microbiol. 2014, 304, 3-13
3. Ohlendorf, B.; Leyers, S.; Krick, A.; Kehraus, S.; Wiese, M.; König, G. M. ChemBioChem 2008, 9, 2997-3003
4. Reichenbach, H.; Höfle, G. In Drug Discovery from Nature; Grabley, S.; Thierecke, R., Eds.; Springer: Heidelberg, 2000; p 173.
5. Trowitzsch, W.; Witte, L.; Reichenbach, H. FEMS Microbiol. Lett. 1981, 12, 257-260
6. Kunze, B.; Trowitzsch-Kinast, W.; Höfle, G.; Reichenbach, H. J. Antibiot. 1992, 45, 147-150
7. Jansen, R.; Sood, S.; Huch, V.; Kunze, B.; Stadler, M.; Müller, R. J. Nat. Prod. 2014, 77, 320-326
8. Irschik, H.; Jansen, R.; Gerth, K.; Höfle, G.; Reichenbach, H. J. Antibiot. 1987, 40, 7-13
9. Gerth, K.; Bedorf, N.; Irschik, H.; Höfle, G.; Reichenbach, H. J. Antibiot. 1994, 47, 23-31
10. Weissman, K. J.; Müller, R. Bioorg. Med. Chem. 2009, 17, 2121-2136
11. Steinmetz, H.; Irschik, H.; Kunze, B.; Reichenbach, H.; Höfle, G.; Jansen, R. Chem.-Eur. J. 2007, 13, 5822-5832
12. Zheng, L.; Yan, X.; Xu, J.; Chen, H.; Lin, W. Appl. Biochem. Microbiol. 2005, 41, 29-33
13. Murata, M.; Legrand, A.-M.; Scheurer, P. J.; Yasumoto, T. Tetrahedron Lett. 1992, 33, 525-526
14. Capon, R. J.; Rooney, F.; Murray, L. M.; Collins, E.; Sin, A. T. R.; Rostas, J. A. P.; Butler, M. S.; Carrol, A. R. J. Nat. Prod. 1998, 61, 660-662
15. Rowan, D. D.; Tapper, B. A. J. Nat. Prod. 1989, 52, 193-195
16. http://www.indexfungorum.org/Names/NamesRecord.asp?RecordID=106582.
17. Cafieri, F.; Fattorusso, E.; Taglialatela-Scafati, O. J. Nat. Prod. 1998, 61, 122-125 and references therein
18. Bano, D.; Ahmad, V. U.; Perveen, S.; Bano, N.; Shafiuddin; Shamel, M. Planta Med. 1987, 53, 117-118
19. Bao, B.; Zhang, P.; Lee, Y.; Hong, J.; Lee, C.-O.; Jung, J. H. Mar. Drugs 2007, 5, 31-39
20. Hu, S.; Tan, R.; Hong, K.; Yu, Z.; Zhu, H. Acta Crystallogr. 2005, E61, 1654-1656
21. Spaepen, S.; Vanderleyden, J.; Remans, R. FEMS Microbiol. Rev. 2007, 31, 425-448
22. Molina-Santiago, C.; Daddaoua, A.; Duque, E.; Ramos, J.-L. Environ. Microbiol. 2014, 16, 1267-1281
23. Dieter, A.; Hamm, A.; Fiedler, H.-P.; Goddfellow, M.; Müller, W. E. G.; Brun, R.; Beil, W.; Bringmann, G. J. Antibiot. 2004, 56, 639-646
24. Xu, F.; Pang, J.; Lu, B.; Wang, J.; Zhang, Y.; She, Z.; Vrijmoed, L. L. P.; Gareth Jones, E. B.; Lin, Y. Chin. J. Chem. 2009, 27, 365-368
25. Schumacher, J. N.; Green, C. R.; Best, F. W.; Newell, M. P. J. Agric. Food Chem. 1977, 25, 310-320
26. Weidel, H.; Ciamician, G. L. Monatsh. Chem. 1881, 1, 279-297
27. Tang, Y.-Q.; Sattler, I.; Thiericke, R.; Grabley, S.; Feng, X.-Z. Eur. J. Org. Chem. 2001, 261-267
28. Motohashi, K.; Inaba, K.; Fuse, S.; Doi, T.; Izumikawa, M.; Khan, S. T.; Takagi, M.; Takahashi, T.; Shin-ya, K. J. Nat. Prod. 2011, 74, 1630-1635
29. Hirano, K.; Kubota, T.; Tsuda, M.; Watanabe, K.; Fromontc, J.; Kobayashia, J. Tetrahedron 2000, 56, 8107-8110
30. Wyatt, M. A.; Wang, W.; Roux, C. M.; Beasley, F. C.; Heinrichs, D. E.; Dunman, P. M.; Magarvey, N. A. Science 2011, 329, 294-296
31. Wyatt, M. A.; Mok, M. C. Y.; Junop, M.; Magarvey, N. A. ChemBioChem 2012, 13, 2408-2415
32. Zimmermann, M.; Fischbach, M. A. Chem. Biol. 2010, 17, 925-930
33. Sun, F.; Cho, H.; Jeong, D.-W.; Li, C.; He, C.; Bae, T. PLoS One 2010, 5, e15703
34. Secor, P. R.; Jennings, L. K.; James, G. A.; Kirker, K. R.; deLancey Pulcini, E.; McInnerney, K.; Gerlach, R. G.; Livinghouse, T.; Hilmer, J. K.; Bothner, B.; Fleckman, P.; Olerud, J. E.; Stewart, P. S. PLoS One 2012, 7, e40973
35. Alvarez, M. E.; White, C. B.; Gregory, J.; Kydd, G. C.; Harris, A.; Sun, H. H.; Gillum, A. M.; Cooper, R. J. Antibiot. 1995, 48, 1165-1167
36. Tatsuta, K.; Tsuchiya, T.; Someno, T.; Umezawa, S. J. Antibiot. 1972, 24, 735-746
37. Tatsuta, K.; Tsuchiya, T.; Umezawa, S. J. Antibiot. 1972, 25, 674-676
38. Tatsuta, K.; Fujimoto, K.; Yamashita, M.; Tsuchiya, T.; Umezawa, S. J. Antibiot. 1973, 26, 606-608
39. Plaga, W.; Stamm, I.; Schairer, H. U. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 11263-11267
40. Meiser, P.; Bode, H. B.; Müller, R. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 19128-19133
41. Pathak, D. T.; Wei, X.; Wall, D. Res. Microbiol. 2012, 163, 579-591 and references therein
42. Mosmann, T. J. Immunol. Methods 1983, 65, 55-63