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Identification and Structure Elucidation of Epoxyjanthitrems from Lolium perenne Infected with the Endophytic Fungus Epichloe festucae var. lolii and Determination of the Tremorgenic and Anti-Insect Activity of Epoxyjanthitrem I.

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.

SUBMITTER: Finch SC 

PROVIDER: S-EPMC7472112 | biostudies-literature | 2020 Aug

REPOSITORIES: biostudies-literature

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Identification and Structure Elucidation of Epoxyjanthitrems from <i>Lolium perenne</i> Infected with the Endophytic Fungus <i>Epichloë festucae</i> var. <i>lolii</i> and Determination of the Tremorgenic and Anti-Insect Activity of Epoxyjanthitrem I.

Finch Sarah C SC   Prinsep Michèle R MR   Popay Alison J AJ   Wilkins Alistair L AL   Webb Nicola G NG   Bhattarai Sweta S   Jensen Joanne G JG   Hawkes Allan D AD   Babu Jacob V JV   Tapper Brian A BA   Lane Geoffrey A GA  

Toxins 20200817 8

Epoxyjanthitrems I-IV (<b>1</b>-<b>4</b>) and epoxyjanthitriol (<b>5</b>) were isolated from seed of perennial ryegrass (<i>Lolium perenne</i>) infected with the endophytic fungus <i>Epichloë festucae</i> var. <i>lolii.</i> 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 f  ...[more]

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