Terpestacin, a toxin produced by Phoma exigua var. heteromorpha, the causal agent of a severe foliar disease of oleander (Nerium oleander L.)

Since 1987, several cytochalasins were isolated from Phoma exigua var. heteromorpha, the causal agent of a severe foliar blight disease of oleander (Nerium oleander L.), and chemically and biologically characterized. Beside their phytotoxic activity, they were in deep investigated for toxic cytological effects on mammalian cells. During the purification process of a large-scale production of cytochalasins A and B, necessary to continue the study on their anticancer activity, a metabolite having a different carbon skeleton compared to that of cytochalasans, was isolated. It was identified as terpestacin, a well-known toxic fungal stestertepenoid, isolated for the first time from P. exigua var. heteromorpha, by spectroscopic investigation (essentially 1D and 2D 1H and 13C-NMR and ESI MS) and optical methods also in comparison with the data available in literature. Terpestacin and some its derivatives (including a natural one, fusaproliferin) were prepared and tested for their biological activity. Terpestacin and fusaproliferin had some inhibitory effects on seed germination of Phelipanche ramosa, whereas none of the compounds caused phytotoxic effects on weed leaves.