Ergogaline, a new ergot alkaloid, produced by Claviceps purpurea: Isolation, identification, crystal structure and molecular conformation

Ladislav Cvak, Teva Pharmaceutical Industries Ltd.
Alexandr Jegorov, Teva Pharmaceutical Industries Ltd.
Petr Sedmera, Academy of Sciences of the Czech Republic
Vladimír Havlíček, Academy of Sciences of the Czech Republic
Jan Ondráček, University of Chemistry and Technology, Prague
Michal Hušák, University of Chemistry and Technology, Prague
Svetlana Pakhomova, University of Chemistry and Technology, Prague
Bohumil Kratochvíl, University of Chemistry and Technology, Prague
Joachim Granzin, Freie Universität Berlin

Abstract

A new peptide ergot alkaloid containing L-homoisoleucine has been isolated from ergot sclerotia of the field-growing parasitic fungus Claviceps purpurea. The molecular and crystal structures have been studied by X-ray analysis [ergogaline monohydrate, monoclinic space group P21 with two molecules per unit cell of the dimensions a = 9.972(1), 6 = 10.902(1) and c = 14.761(1) Å, β = 94.05(1)°] and compared with the structures in solution as determined by 2D NMR spectroscopy.