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Mass spectrometry of orellanine, a mushroom toxin, and of related bipyridine-N-oxides

1989; Wiley; Volume: 18; Issue: 1 Linguagem: Inglês

10.1002/bms.1200180102

2376-3868

Jean-Michel Richard, J. Ulrich,

Insect and Pesticide Research

The electron impact (EI) mass spectrometry of orellanine, the toxin of several Cortinarius mushrooms, is reported and compared to that of related bipyridine-N-oxides. In constrast to results previously published by other authors, orellanine is found to lose a hydroxyl radical easier than an oxygen atom in a first step, as attested by the occurrence of a metastable ion. Metastable ion kinetic energy spectra show that the molecular ion of each 2,2′-bipyridine-N,N′-dioxide studied loses an OH-radical but no oxygen atom in a first step. The elimination of oxygen atoms observed by other authors by EI or chemical ionization (CI) mass spectrometry of orellanine is attributed to a pyrolytic process of degradation before ionization. These results do not support the hypothesis of the existence of intramolecular hydrogen bonds in the molecule of orellanine.