l-Phenylalanine Alters the Privileged Secondary Metabolite Production in the Marine-Derived Fungus F1-1.

The effects of a single-amino-acid culture strategy on secondary metabolite production in the marine-derived fungus F1-1 were investigated by culturing the fungus in GPY medium supplemented or not supplemented with l-phenylalanine. A suite of secondary metabolites, including seven terpenoids (-) and one polyketide (), among which are four new compounds, harziandione A (), cyclonerodiols A and B (, ), and trichodermaerin A (), were isolated from the GPY medium without l-phenylanine, whereas 18 aromatic compounds (-), including six new compounds, trichoderolides A-F (, , and -), were isolated from the culture grown in the GPY medium with l-phenylalanine. The structures of the new compounds were determined by high-resolution mass spectrometry, NMR spectroscopic analysis, optical rotation calculations, chemical methods, and X-ray crystallography. Compounds , , , and exhibited cytotoxic activities against MDA-MB-435 human melanocyte cancer cells. Compound was cytotoxic to A549 adenocarcinomic human alveolar basal epithelial cells.