Coniosetin, a novel tetramic acid antibiotic from Coniochaeta ellipsoidea DSM 13856

Journal of Antibiotics

Volumn 56, Issue 2, 2003, Pages 114-122

  Segeth, Marian Paul ^a   Bonnefoy, Alain ^b   Brönstrup, Mark ^a   Knauf, Martin ^c   Schummer, Dietmar ^a   Toti, Luigi ^a   Vértesy, László ^a   Wetzel Raynal, Marie Cécile ^b   Wink, Joachim ^a   Seibert, Gerhard ^a  

^a SANOFI AVENTIS DEUTSCHLAND GMBH   (Germany)

^b Hoechst Marion Roussel   (France)

^c UFAG Laboratorien AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

ALIPHATIC COMPOUND; AMPHOTERICIN B; ANTIBIOTIC AGENT; CARBONYL DERIVATIVE; CONIOSETIN; ERYTHROMYCIN; OFLOXACIN; OXACILLIN; PENICILLIN G; TEICOPLANIN; TETRACYCLINE; TETRAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIFUNGAL ACTIVITY; ARTICLE; ASCOMYCETES; CIRCULAR DICHROISM; CONCENTRATION (PARAMETERS); CONIOCHAETA ELLIPSOIDEA; CONTROLLED STUDY; CULTURE MEDIUM; DATA ANALYSIS; DRUG STRUCTURE; FUNGUS CULTURE; GRAM NEGATIVE BACTERIUM; MALT; MASS SPECTROMETRY; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; OAT; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; STRUCTURE ANALYSIS;

CONIOCHAETA ELLIPSOIDEA; STAPHYLOCOCCUS AUREUS;

EID: 0345700230     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.7164/antibiotics.56.114     Document Type: Article

References (28)

1. LEVIN, S. A. & V. ANDREASEN: Disease transmission dynamics and the evolution of antibiotic resistance in hospitals and communal settings. Proc. Natl. Acad. Sci. USA 96: 800-801, 1999
2. BRONSON, J. J. & J. F. BARRETT: Quinolone, everninomycin, glycylcycline, carbapenem, lipopeptide and cephem antibacterials in clinical development. Curr. Med. Chem. 2001: 1775-1793, 2001
3. WANG, H.-J.; J. B. GLOER, J. A. SCOTT & D. MALLOCH: Coniochaetones A and B: new antifungal benzopyranones from the coprophilous fungus Coniochaeta saccardoi. Tetrahedron Lett. 36: 5847-5850, 1995
4. FUJIMOTO, H.; M. INAGAKI, Y. SATOH, E. YOSHIDA & M. YAMAZAKI: Monoamine oxidase-inhibitory components from an ascomycete. Coniochaeta tetraspora. Chem. Pharm. Bull. 44: 1090-1092, 1996
5. JOHNSTON, E. R.; M. J. DELLWO & J. HENDRIX: Quantitative 2D exchange spectroscopy using time-proportional phase incrementation. J. Magn. Reson. 66: 399-409, 1986
6. 1H spin-spin coupling constants in proteins. Biochem. Biophys. Res. Commun. 113: 967-974, 1983
7. PIANTINI, U.; O. W. SORENSEN & R. R. ERNST: Multiple quantum filters for elucidating NMR coupling networks. J. Am. Chem. Soc. 104: 6800, 1982
8. RANCE, M.; O. W. SORENSEN, G. BODENHAUSEN, G. WAGNER, R. R. ERNST & K. WÜTHRICH: Improved spectral resolution in COSY proton NMR spectra of proteins via double quantum filtering. Biochem. Biophys. Res. Commun. 117: 479-485, 1983
9. JEENER, J.; B. H. MEIER, P. BACHMANN & R. R. ERNST: Investigation of exchange processes by two-dimensional NMR spectroscopy. J. Chem. Phys. 71: 4546-4553, 1979
10. KUMAR, A.; R. R. ERNST & K. WUETHRICH: A two-dimensional nuclear Overhauser enhancement (2D NOE) experiment for the elucidation of complete proton-proton cross-relaxation networks in biological macromolecules. Biochem. Biophys. Res. Commun. 95: 1-6, 1980
11. BOTHNER-BY, A. A.; R. L. STEPHENS, J. LEE, C. D. WARREN & J. W. JEANLOZ: Structure determination of a tetrasaccharide: Transient Nuclear Overhauser Effects in the rotating frame. J. Am. Chem. Soc. 106: 811-813, 1984
12. BAX, A. & S. SUBRAMANIAN: Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy. J. Magn. Reson. 67: 565-569, 1986
13. 13C Assignments from sensitivity-enhanced detection of heteronuclear multiple-bond connectivity by two-dimensional multiple quantum NMR. J. Am. Chem. Soc. 108: 2093-2094, 1986
14. LUMLEY, T. C.; S. P. ABBOTT & R. S. CURRAH: Microscopic Ascomycetes isolated from rotting wood in the boreal forest. Mycotaxon LXXIV: 395-414, 2000
15. VÉRTESY, L.; M. KNAUF, A. MARKUS, L. TOTI, M.-C. RAYNAL & F. FASSY: Coniosetin and derivatives thereof, production method, and therapeitic use. PCT Int. Appl. WO 0246152 A2, June 13th, 2002
16. SINGH, S. B.; D. L. ZINK, M. A. GOETZ, A. W. DOMBROWSKI, J. D. POLISHOOK & D. J. HAZUDA: Equisetin and a novel opposite stereochemical homolog phomasetin, two fungal metabolites as inhibitors of HIV-1 integrase. Tetrahedron Lett. 39: 2243-2246, 1998
17. ROYLES, B. J. L.: Naturally occurring tetramic acids: Structure, isolation, and Synthesis. Chem. Rev. 95: 1981-2001, 1995
18. HOPMANN, C.; M. KURZ, M. BRÖNSTRUP, J. WINK & D. LEBELLER: Isolation and structure elucidation of vancoresmycin - a new antibiotic from Amycolatopsis sp. ST 101170. Tetrahedron Lett. 43: 435-438, 2002
19. OSTERHAGE, C.; R. KAMINSKY, G. M. KÖNIG & A. D. WRIGHT: Ascosalipyrrolidinone A, an antimicrobial alkaloid, from the obligate marine fungus Ascochyta salicorniae. J. Org. Chem. 65: 6412-6417, 2000
20. HÖLTZEL, A.; M. G. GÄNZLE, G. J. NICHOLSON, W. P. HAMMES & G. JUNG: The first low molecular weight antibiotic from lactic acid bacteria: reutericyclin, a new tetramic acid. Angew. Chem. Intern. Ed. 39: 2766-2768, 2000
21. TANAKA, A.; T. OHYAMA, Y. KAWAMURA, S. MIYAKOSHI, T. HOSOYA & S. TAKAHASHI: F-10778, a new antifungal antibiotic produced by the discomycete Tapesia sp. Annu. Rep. Sankyo Res. Lab. 49: 135-141, 1997
22. SATA, N. U.; S.-I. WADA, S. MATSUNAGA, S. WATABE & R.W. M. Van SOEST: Rubrosides A-H, new bioactive tetramic acid glycosides from the marine sponge Siliquariaspongia japonica. J. Org. Chem. 64: 2331-2339, 1999
23. STROBEL, G.; J. HARPER, E. LOBKOVSKY & J. CLARDY: Cryptocin, a potent tetramic acid antimycotic from the endophytic fungus Cryptosporiopsis cf. quercina. Organic Letters 2: 767-770, 2000
24. SUZUKI, S.; T. HOSOE, K. NOZAWA, K.-I. KAWAI. YAGUCHI & S.-I. UDAGAWA: Antifungal substances against pathogenic fungi, talaroconvolutins, from Talaromyces convolutus. J. Nat. Prod. 63: 768-772, 2000
25. HASHIDOKO, Y.; T. NAKAYAMA, Y. HOMMA & S. TAHARA: Structure elucidation of xanthobaccin A, a new antibiotic produced from Stenotrophomonas sp. strain SB-K88. Tetrahedron Lett. 40: 2957-2960, 1999
26. SUGIE, Y.; K. A. DEKKER, T. INAGAKI, Y.-J. Kim, T. SAKAKIBARA, S. SAKEMI, A. SUGIURA, L. BRENNAN, J. DUIGNAN, J. A. SUTCLIFFE, & Y. KOJIMA: A novel antibiotic CJ-17,572 from a fungus, Pezicula sp. J. Antibiotics 55: 19-24, 2002
27. SUGIE, Y.; S. INAGAKI, Y. KATO, H. NISHIDA, C.-H. PANG, T. SAITO, S. SAKEMI, F. DIB-HAJJ, J. P. MUELLER, J. SUTCLIFFE & Y. KOJIMA: CJ-21,058, a new SecA inhibitor isolated from a fungus. J. Antibiotics 55: 25-29, 2002
28. KÖNIG, T.; A. KAPUS & B. SARKADI: Effect of equisetin on rat liver mitochondria: evidence for inhibition of substrate anion carriers of the inner membrane. J. Bioenerg. Biomembr. 25: 537-545, 1993