The isolation, identification, and bioassay of the antifungal metabolites produced by Monocillium nordinii

Abstract

The metabolites produced when Monocillium nordinii (Bourchier) W. Gams, a destructive mycoparasite of pine stem rusts, is grown in liquid culture have been separated and identified. The metabolites include the known compound monorden (1) and five new substances, monocillin I (2), monocillin II (4), monocillin III (3), monocillin IV (5), and monocillin V (6). Structural assignments and chemical correlations of the five new compounds are reported and the absolute configuration of monorden is assigned. The antifungal spectra of the three major metabolites are reported. Monorden and monocillin I show pronounced activity against a wide variety of fungi, including Ceratocystis ulmi, the cause of Dutch elm disease. Extraction of the mycelium yielded averufin (13), along with a pigment C18H12O6, as yet unidentified.