Identification and structure elucidation of epoxyjanthitrems from Lolium perenne infected with the endophytic fungus Epichloë festucae var. lolii and determination of the tremorgenic and anti-insect activity of epoxyjanthitrem I.
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© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
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.
Citation
Finch, S. C., Prinsep, M. R., Popay, A. J., Wilkins, A. L., Webb, N. G., Bhattarai, S., … Lane, G. A. (2020). Identification and structure elucidation of epoxyjanthitrems from Lolium perenne infected with the endophytic fungus Epichloë festucae var. lolii and determination of the tremorgenic and anti-insect activity of epoxyjanthitrem I. Toxins (Basel), 12(8). https://doi.org/10.3390/toxins12080526