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A series of studies was conducted to test the antifungal activity of clavicipitaceous endophytes and to identify potential fungal inhibitors in this symbiotic infection. A diverse group of endophytes was screened for antifungal activity using organic extracts from liquid fermentation cultures. Fungal inhibitors were purified from fermentation cultures of Epichloë festucae using a bioassay-directed extraction with Cryphonectria parasitica as the test organism. Compounds shown to have antifungal activity were subsequently identified using NMR and GC-MS. Extracts from a wide range of fungal isolates had various degrees of antifungal activity, but the greatest antifungal activity was observed in E. festucae and Neotyphodium tembladerae. Three types of inhibitors were isolated from a batch culture of E. festucae, including several indole derivatives, a sesquiterpene, and a diacetamide. Among the indole derivatives, indole-3 …