On the New Peptide-Type Ergot Alkaloids, Ergosecaline and Ergosecalinine

Bulletin of the Agricultural Chemical Society of Japan
1959.0

Abstract

Formerly, H. Rassbach et al. and the authors reported ergometrine formation in saprophytic cultures of Claviceps purpurea. The authors isolated various alkaloids (peptide-type alkaloids, ergometrine, ergometrinine, agroclavine, secaclavine, and a new water-soluble alkaloid) from the saprophytic culture (mycelium and filtrate) of a C. purpurea strain from Spanish rye ergot and from the ergot itself. The new water-soluble alkaloid, named ergosecalinine (presumed to be a peptide-type alkaloid with an isolysergic acid nucleus), was found via paper partition chromatography to be interconvertible with another unknown water-soluble alkaloid (ergosecaline) in both the ergot and fungal culture. The physicochemical properties of ergosecalinine were characterized, including melting point, optical rotation, elemental analysis, spectral data (UV, IR), solubility, and hydrolysis products (yielding pyruvic acid and lysergic acid on alkaline hydrolysis, and valine on acid hydrolysis). It was assumed that ergosecaline and ergosecalinine share a common structure. Additionally, the alkaloid chanoclavine was found to be identical to secaclavine in paper chromatographic behavior and IR spectrum. This work was financially supported in part by a Research Grant from the Ministry of Education.

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