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Mass spectrometry of orellanine, a mushroom toxin, and of related bipyridine‐ N ‐oxides
Author(s) -
Richard JeanMichel,
Ulrich Jacques
Publication year - 1989
Publication title -
biomedical and environmental mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0887-6134
DOI - 10.1002/bms.1200180102
Subject(s) - chemistry , mass spectrometry , intramolecular force , electron ionization , mass spectrum , molecule , ion , oxygen , photochemistry , hydrogen atom , chemical ionization , homolysis , ionization , radical , stereochemistry , organic chemistry , alkyl , chromatography
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.