Pterulinic acid and pterulone, two novel inhibitors of NADH:ubiquinone oxidoreductase (complex I) produced by a Pterula species. II. Physico-chemical properties and structure elucidation.
The structures of two novel fungal antibiotics, isolated from a Pterula species, that interfere with the NADH:ubiquinone oxidoreductase and inhibit the respiration of eucaryotes, were determined by spectroscopic techniques. Both compounds, pterulinic acid (1a) and pterulone (2), contain a 1-benzoxepin ring system and are chlorinated. Pterulinic acid (1a), which was obtained as a 1:5 inseparable mixture of the two isomers (Z)-1a and (E)-1a, in addition contains a furan. Their structures were determined by mass spectrometry and NMR spectroscopy, and 2D heteronuclear correlation experiments permitted the assignment of all NMR signals.
Engler
M
M
LB Biotechnologie der Universität, Kaiserslautern, FRG.
Anke
T
T
Sterner
O
O
D000085:Acetates / Q000737:chemistry*; D000935:Antifungal Agents / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010082:Oxepins; D013237:Stereoisomerism
D000085:Acetates; D000935:Antifungal Agents; D001572:Benzofurans; D010082:Oxepins; C106751:pterulinic acid; C106752:pterulone