Role of the δ 8 double bond of agroclavine in lysergic acid amide biosynthesis byClaviceps purpurea

Abstract

Agroclavine, given to actively-growing sclerotial tissue of a strain of Claviceps purpurea which can not normally elaborate ergot alkaloids, was transformed by this tissue into lysergic acid amide with overall efficiency of approximately 40%. By contrast, festuclavine (8,9-dihydro-agroclavine) was not transformed, indicating specificity in the mechanism of lysergyl biosynthesis.

Mass spectral characterization of ergot alkaloids by electrospray ionization, hydrogen/deuterium exchange, and multiple stage mass spectrometry: usefulness of precursor ion scan experiments

“…1). Agroclavine and elymoclavine belong to the first group and are generally reported as precursor compounds for the other two groups of ergot alkaloids in their biogenetic pathways 5. These alkaloids are not used pharmacologically, but agroclavine is a powerful uterine stimulant, and many of the ergot alkaloids are prolactin release inhibitors 6.…”