The chemistry of the blue stain fungi. Part 3. Some metabolites of Ceratocystisminor (Hedgcock) Hunt

Abstract

The metabolites formed in still cultures by Ceratocystisminor, one of the fungal species associated with the blue stain disease of pine, have been isolated and identified as ceratenolone (5), 6,8-dihydroxy-3-methylisocoumarin (2), 8-hydroxy-6-methoxy-3-methylisocoumarin (8), 3,4-dihydro-6,8-dihydroxy-3-methylisocoumarin (10), 3,4-dihydro-3-methyl-3,6,8-trihydroxy-3-methylisocoumarin (12), 3,4-dihydro-3-methyl-3,4,6,8-tetrahydroxyisocoumarin (13), and succinic acid. Ceratenolone (5), a new type of natural product, forms an intensely blue chelate with ferric ions. This chelate may be responsible for the blue coloration of the wood of pine infected by Ceratocystisminor.