Festucine, an alkaloid from tall fescue (Festuca arundinacea Schreb.): Chemistry of the functional groups

Abstract

The most abundant alkaloid of tall fescue hay, termed festucine by the authors, was isolated by preparative paper chromatography. The empirical formula of the free base is C₈H₁₄N₂O, and the molecular weight is 154. One nitrogen of festucine is tertiary, the other secondary. The alkaloid also contains a cyclic ether which can be cleaved by treatment with hydrochloric acid at 160°. The chemical evidence for festucine is consistent with its structural formulation as a positional isomer of loline, a pyrrolizidine alkaloid from the seed of a related grass (Lolium cuneatum Nevski).