Identification and Structure Elucidation of Janthitrems A and D from Penicillium janthinellum and Determination of the Tremorgenic and Anti-Insect Activity of Janthitrems A and B

New compounds, 11,12-epoxyjanthitrem B (1) and 11,12-epoxyjanthitrem C (4), were isolated from Penicillium janthinellum and given the trivial names janthitrem A and janthitrem D, respectively. The known compounds janthitrem B (2) and janthitrem C (3) were also isolated, and NMR assignments were made for all four compounds. This showed that the previously published NMR assignments for 3 needed considerable revision. 1 and 2 were used as model compounds for the more complex, and highly unstable, epoxyjanthitrems that have been isolated from perennial ryegrass infected with the AR37 endophyte and which contain an epoxide group analogous to that of 1. Both 1 and 2 induced tremors in mice and reduced weight gain and food consumption of porina (Wiseana cervinata) larvae, although 1 showed greater potency. This shows the importance of the epoxy group and suggests that epoxyjanthitrems are likely to be involved in the observed effects of the AR37 endophyte on livestock and insects.