Terpendole M, a novel indole-diterpenoid isolated from Lolium perenne infected with the endophytic fungus Neotyphodium lolii.
Terpendole M (1), a novel indole-diterpenoid, was isolated from perennial ryegrass (Lolium perenne) infected with the endophytic fungus Neotyphodium lolii. It was identified as 14alpha-hydroxyterpendole C by NMR and mass spectral techniques. The known indole-diterpenoids paspaline (3) and 13-desoxypaxilline (4) were also isolated from perennial ryegrass for the first time. Terpendole M was less tremorgenic than terpendole C (2) in a standard mouse bioassay. These findings provide clues to the biogenesis of the lolitrem neurotoxins, and information on the structure-activity relationships within the indole-diterpenoids.
Gatenby
W A
WA
New Zealand Pastoral Agriculture Research Institute Ltd., Ruakura Agricultural Research Centre, Private Bag 3123, Hamilton, New Zealand.
Munday-Finch
S C
SC
Wilkins
A L
AL
Miles
C O
CO
D000164:Acremonium / Q000472:pathogenicity*; D000818:Animals; D004224:Diterpenes / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D005260:Female; D007211:Indoles / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D008129:Lolium / Q000737:chemistry* / Q000382:microbiology*; D051379:Mice; D008958:Models, Molecular; D008968:Molecular Conformation; D009498:Neurotoxins / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity; D013329:Structure-Activity Relationship; D014202:Tremor / Q000139:chemically induced*
D004224:Diterpenes; D007211:Indoles; D009498:Neurotoxins; C092163:terpendole C