LYSERGIC-ACID AMIDE DERIVATIVES FROM BALANSIA-EPICHLOE AND BALANSIA-CLAVICEPS (CLAVICIPITACEAE)

Clavicipitaceous systemic phytopathogens, Balansia epichloë (Weese) Diehl, B. henningsiana (Möller) Diehl, B. strangulans (Mont.) Diehl, Myriogenospora atramentosa Berk, and Curt., and Epichloe typhina Fries, have been implicated in unexplained toxic syndromes occurring in cattle grazed on infected pasture grasses (1-5). The occurrence of the genus Claviceps and the role of ergot alkaloids in similar livestock problems have been well documented (6-9). The taxonomic relationships between Balansia and Claviceps (10, 11) and the association of Balansia with these “ergot-like” symptoms (1-5) prompted investigations into the possibility that Balansia may produce the ergoline-type alkaloids (3, 4, 12). Bacon et al. (13) demonstrated that B. epichloë, B. strangulans, B. henningsiana, and B. claviceps produced ergot alkaloids in laboratory cultures. We now report the chemical identification of the ergot alkaloids from B. epichloë as: chanoclavine I, isochanoclavine I, agroclavine, elymoclavine, penniclavine, ergonovine, ergonovinine, and two other clavine alkaloids (uv, m e+) that have molecular ions M+240 and that do not correspond with festuclavine, pyroclavine, or costaclavine on co-chromatography. Also, we report on the isolation and identification of chanoclavine I. ergonovine, and ergonovinine from cultures of B. claviceps. Until now, no lysergic acid derivatives had been found in fungi outside the genus Claviceps (14).2 The identification of ergonovine and ergonovinine from B. epichloë and B. claviceps suggests that other members of the Balansiae are capable of ergoline biosynthesis. Thus, members of the genus Balansia may have caused the unexplained incidences of “Clavicepsor ergot-like” syndromes in livestock that had ingested infected pasture grass. © 1979, American Chemical Society. All rights reserved.