Abstract
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.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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3',5'-Cyclic-AMP Phosphodiesterases / antagonists & inhibitors*
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Amaranthus / drug effects
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Animals
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Brain / drug effects
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Calmodulin / antagonists & inhibitors*
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Cattle
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Cyclic Nucleotide Phosphodiesterases, Type 1
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / isolation & purification*
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Enzyme Inhibitors / pharmacology
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Fungi / chemistry*
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Heterocyclic Compounds, 1-Ring
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Inhibitory Concentration 50
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Lactones / chemistry
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Lactones / isolation & purification*
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Lactones / pharmacology
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Molecular Conformation
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Seeds / drug effects
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Zea mays
Substances
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Calmodulin
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Enzyme Inhibitors
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Heterocyclic Compounds, 1-Ring
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Lactones
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herbarumin I
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herbarumin II
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herbarumin III
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3',5'-Cyclic-AMP Phosphodiesterases
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Cyclic Nucleotide Phosphodiesterases, Type 1