Abstract
In the course of our continuing search for new bioactive fungal natural products, analysis of an ethyl acetate extract from cultures of a fungal isolate obtained from a black pyrenomycete stroma found on a dead hardwood branch at Torreya State Park, Florida (Fusarium merismoides; MYC-1368) was undertaken. This extract was selected for investigation because it showed antifungal activity against Aspergillus flavus and Fusarium verticillioides, and antiinsectan effects against fall armyworm. Chemical studies of this extract yielded several new peptides, as well as the known compounds equisetin and 11-keto-9(E),12(E)-octadecadienoic acid. The structures of the new peptides were assigned by analysis of 2D NMR data in conjunction with HRESITOFMSMS, GCMS amino acid analysis, and Marfey's method. Each new peptide analogue consists of a fatty acyl component connected to a Val-Pro-MeIle sequence, terminating in a reduced Pro (prolinol) unit that is acetylated in some cases. The prolinol unit is rare, as it is reportedly present in only three other natural products and their analogues, scalusamides A-C, viriditin-all from fungal sources-and actinonin, which is produced by Streptomyces roseopallidus and was the first reported source of a natural product containing an L-(-)-prolinol unit. These prolinol-containing compounds were reported to have antibacterial, antifungal, and/or cytotoxic activities. The most abundant component isolated in the present study caused a reduced growth rate in assays against fall armyworm.
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