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J Antibiot (Tokyo) ; 56(2): 114-22, 2003 Feb.
Article in English | MEDLINE | ID: mdl-12715870

ABSTRACT

The coprophilic ascomycete Coniochaeta ellipsoidea DSM 13856 forms the new antibiotic coniosetin (1) in surface cultures grown on a medium containing malt extract and oatmeal. The structure of the compound C25H35NO4, MW 413, was determined by 2D-NMR and mass spectrometric studies. Coniosetin belongs to the class of tetramic acids; it consists of a substituted aliphatic bicyclic ring system linked to a tetramic acid subunit through a carbonyl center. The absolute configuration was determined by measuring its circular dichroism spectrum and comparing the data with those of equisetin. Coniosetin has a pronounced antibacterial and antifungal action, inhibiting even multi drug-resistant strains of Staphylococcus aureus at a concentration of 0.3 microg/ml, though it is inactive against Gram-negative bacteria.


Subject(s)
Anti-Bacterial Agents/chemistry , Ascomycota/metabolism , Naphthalenes/chemistry , Pyrrolidinones/chemistry , Anti-Bacterial Agents/biosynthesis , Anti-Bacterial Agents/isolation & purification , Anti-Bacterial Agents/pharmacology , Ascomycota/chemistry , Chromatography, High Pressure Liquid , Circular Dichroism , Fermentation , Microbial Sensitivity Tests , Molecular Structure , Molecular Weight , Naphthalenes/isolation & purification , Naphthalenes/pharmacology , Nuclear Magnetic Resonance, Biomolecular , Optical Rotation , Pyrrolidinones/isolation & purification , Pyrrolidinones/metabolism , Pyrrolidinones/pharmacology , Spectrometry, Mass, Fast Atom Bombardment , Spectrophotometry, Infrared , Spectrophotometry, Ultraviolet , Staphylococcus aureus/metabolism
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