Coniosetin, a novel tetramic acid antibiotic from Coniochaeta ellipsoidea DSM 13856.
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.
Segeth
Marian Paul
MP
Aventis Pharma Deutschland GmbH, Drug Innovation & Approval, Industriepark Höchst, D-65926 Frankfurt/Main, Germany.
Bonnefoy
Alain
A
Brönstrup
Mark
M
Knauf
Martin
M
Schummer
Dietmar
D
Toti
Luigi
L
Vértesy
László
L
Wetzel-Raynal
Marie-Cécile
MC
Wink
Joachim
J
Seibert
Gerhard
G
D000900:Anti-Bacterial Agents / Q000096:biosynthesis / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D001203:Ascomycota / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D002942:Circular Dichroism; D005285:Fermentation; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D008970:Molecular Weight; D009281:Naphthalenes / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D019906:Nuclear Magnetic Resonance, Biomolecular; D009904:Optical Rotation; D011760:Pyrrolidinones / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism / Q000494:pharmacology; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013211:Staphylococcus aureus / Q000378:metabolism
D000900:Anti-Bacterial Agents; D009281:Naphthalenes; D011760:Pyrrolidinones; C474181:coniosetin