Identification and Structure Elucidation of Epoxyjanthitrems fromInfected with the Endophytic Fungusvar.and Determination of the Tremorgenic and Anti-Insect Activity of Epoxyjanthitrem I.

Abstract

Epoxyjanthitrems I-IV (-) and epoxyjanthitriol () were isolated from seed of perennial ryegrass () infected with the endophytic fungusvar.Although structures for epoxyjanthitrems I-IV have previously been proposed in the literature, this is the first report of a full structural elucidation yielding NMR (Nuclear magnetic resonance) assignments for all five epoxyjanthitrem compounds, and additionally, it is the first isolation of epoxyjanthitriol (). Epoxyjanthitrem I induced tremors in mice and gave a dose dependent reduction in weight gain and feeding for porina (), a common pasture pest in New Zealand. These data suggest that epoxyjanthitrems are involved in the observed effects of the AR37 endophyte on livestock and insect pests.