Abstract
Epoxyjanthitrems I–IV (1–4) and epoxyjanthitriol (5) were isolated from seed of perennial ryegrass (Lolium perenne) infected with the endophytic fungus Epichloë festucae var. lolii. 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 (5). Epoxyjanthitrem I induced tremors in mice and gave a dose dependent reduction in weight gain and feeding for porina (Wiseana cervinata), 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.
Highlights
IntroductionMany of the world’s grasses, including the agriculturally important perennial ryegrass (Lolium perenne L.) and tall fescue (Festuca arundinacea Schreb.) are infected with Epichloë (formerly Neotyphodium, formerly Acremonium) [1] endophytic fungi
Many of the world’s grasses, including the agriculturally important perennial ryegrass (Lolium perenne L.) and tall fescue (Festuca arundinacea Schreb.) are infected with Epichloë [1] endophytic fungi
Not producing peramine and being ineffective against adult Argentine stem weevil, AR37 has a strong effect on reducing Argentine stem weevil larval damage [10], has an effect on adult African black beetle [11] as well as effects on porina (Wiseana cervinata) [12,13], root aphid [11,14,15] and pasture mealybug (Balanococcus poae) [16]
Summary
Many of the world’s grasses, including the agriculturally important perennial ryegrass (Lolium perenne L.) and tall fescue (Festuca arundinacea Schreb.) are infected with Epichloë (formerly Neotyphodium, formerly Acremonium) [1] endophytic fungi. In addition to these beneficial secondary metabolites, the naturally-occurring (common-toxic) endophyte-perennial ryegrass association expresses lolitrem B (10), a secondary metabolite which is the cause of ryegrass staggers, a neurological condition of grazing animals responsible for major production losses and farm management issues for farmers [4] This association expresses ergovaline, which in addition to its anti-insect effects is responsible for heat stress in grazing animals [5]. AR1 endophyte-infected ryegrass suffers damage by African black beetle and a root aphid (Aploneura lentisci), which reduces productivity and persistence of ryegrass [8,9] Another commercial endophyte, AR37, shows much broader effects against common insect pasture pests. Not producing peramine and being ineffective against adult Argentine stem weevil, AR37 has a strong effect on reducing Argentine stem weevil larval damage [10], has an effect on adult African black beetle [11] as well as effects on porina (Wiseana cervinata) [12,13], root aphid [11,14,15] and pasture mealybug (Balanococcus poae) [16]
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