Structure Elucidation of Lolitrem F, a Naturally Occurring
Stereoisomer of the Tremorgenic Mycotoxin Lolitrem B, Isolated
from <i>Lolium perenne</i> Infected with <i>Acremonium lolii</i>
Sarah C. Munday-Finch
Alistair L. Wilkins
Christopher O. Miles
Richard M. Ede
Ralph A. Thomson
10.1021/jf950396b.s001
https://acs.figshare.com/articles/journal_contribution/Structure_Elucidation_of_Lolitrem_F_a_Naturally_Occurring_Stereoisomer_of_the_Tremorgenic_Mycotoxin_Lolitrem_B_Isolated_from_i_Lolium_perenne_i_Infected_with_i_Acremonium_lolii_i_/3679353
A new lolitrem, lolitrem F (<b>2</b>), was isolated from
endophyte-infected perennial ryegrass. Its structure
was shown by mass spectrometry and one- and two-dimensional NMR
spectroscopy to be a 31,35-<i>cis</i>-fused isomer of lolitrem B. Base-catalyzed
epimerization of <b>2</b> and lolitrem B (<b>1</b>) afforded
their
31-epimers (<b>4</b> and <b>3</b>, respectively).
Comparison with spectral data for <b>1</b> and
31-<i>epi</i>-lolitrem B (<b>3</b>)
established lolitrem F to be 35<i>-epi</i>-lolitrem B.
Compounds <b>1</b>, <b>2</b>, and <b>4</b> were
equally tremorgenic in
a mouse bioassay, but <b>3</b> was nontremorgenic.
Base-catalyzed exchange of H-31 was found to permit
efficient incorporation of deuterium (and potentially, therefore, of
tritium) into <b>1</b> and <b>3</b>.
Keywords: <i>Acremonium lolii</i>; <i>Lolium perenne</i>;
endophyte; lolitrem; tremor; ryegrass staggers;
neurotoxin; mycotoxin
1996-09-18 00:00:00
Tremorgenic Mycotoxin Lolitrem B
Acremonium lolii
lolitrem B
lolitrem F
NMR
Lolium perenne Infected