A new phytotoxic nonenolide from Phoma herbarum.
Reinvestigation of the fermentation broth and mycelium of the fungus Phoma herbarum led to the isolation of a new phytotoxic nonenolide, namely, (7R,9R)-7-hydroxy-9-propyl-5-nonen-9-olide, which was designated with the trivial name herbarumin III (3). The known compounds herbarumins I (1) and II (2) were also obtained. The structure of 3 was elucidated by spectroscopic methods and molecular modeling. Compounds 1-3 interacted with bovine-brain calmodulin and inhibited the activation of the calmodulin-dependent enzyme cAMP phosphodiesterase.
Rivero-Cruz
José Fausto
JF
Departamento de Farmacia, Facultad de Química, Universidad Nacional Autónoma de México, México D.F. 04510, México.
Macías
Martha
M
Cerda-García-Rojas
Carlos M
CM
Mata
Rachel
R
D015105:3',5'-Cyclic-AMP Phosphodiesterases / Q000037:antagonists & inhibitors*; D027721:Amaranthus / Q000187:drug effects; D000818:Animals; D001921:Brain / Q000187:drug effects; D002147:Calmodulin / Q000037:antagonists & inhibitors*; D002417:Cattle; D054677:Cyclic Nucleotide Phosphodiesterases, Type 1; D004791:Enzyme Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D005658:Fungi / Q000737:chemistry*; D006573:Heterocyclic Compounds, 1-Ring; D020128:Inhibitory Concentration 50; D007783:Lactones / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012639:Seeds / Q000187:drug effects; D003313:Zea mays
D002147:Calmodulin; D004791:Enzyme Inhibitors; D006573:Heterocyclic Compounds, 1-Ring; D007783:Lactones; C462121:herbarumin I; C462120:herbarumin II; C477617:herbarumin III; D015105:3',5'-Cyclic-AMP Phosphodiesterases; D054677:Cyclic Nucleotide Phosphodiesterases, Type 1