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). 2020 Aug 17;12(8):526. doi: 10.3390/toxins12080526.

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.

Keywords: AR37; Epichloë festucae var. lolii; endophyte; epoxyjanthitrem; porina; ryegrass staggers; tremorgen.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Disease Models, Animal
  • Endophytes / chemistry*
  • Epichloe / chemistry*
  • Female
  • Host Microbial Interactions
  • Insecta / drug effects*
  • Lolium / microbiology*
  • Mice
  • Mycotoxins / chemistry*
  • Mycotoxins / pharmacology*
  • New Zealand
  • Tremor / chemically induced*

Substances

  • Mycotoxins

Supplementary concepts

  • Epichloe festucae