New Hynapene Analogs from a Fungicolous Isolate of Penicillium chrysogenum

During our ongoing studies of mycoparasitic and fungicolous fungi as sources of new bioactive secondary metabolites, an isolate of Penicillium chrysogenum (MYC 2111) collected from the surface of black stromata of a pyrenomycete found on a dead hardwood branch near Onomea Bay, Hawaii, was investigated owing to the significant activity of its fermentation extract in assays against fall armyworm. The culture was identified based on its micromorphology and sequence analysis revealed the closest matches (99%) as P. chrysogenum. Data for the isolate have been deposited in GenBank under accession number KFO 11475. Chromatographic separation of the extract resulted in isolation of two new analogues of the hynapene class. Previously described members of this class, which were isolated from other Penicillium spp. (hynapenes A, B, and C) reportedly display anticoccidial activity. The two new metabolites were identified as hynapene analogues on the basis of their NMR and HRESITOFMS data in comparison with those reported for hynapenes A-C. Their structures and relative configurations were assigned by analysis of 2D NMR data.