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Analysis of fungal cyclopentenone derivatives from Hygrophorus spp. by liquid chromatography/electrospray‐tandem mass spectrometry
Author(s) -
Lübken Tilo,
Arnold Norbert,
Wessjohann Ludger,
Böttcher Christoph,
Schmidt Jürgen
Publication year - 2006
Publication title -
journal of mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 1076-5174
DOI - 10.1002/jms.996
Subject(s) - chemistry , cyclopentenone , electrospray , tandem mass spectrometry , mass spectrometry , chromatography , mass spectrum , dissociation (chemistry) , stereochemistry , organic chemistry
Fruitbodies of the genus Hygrophorus (Basidiomycetes) contain a series of anti‐biologically active compounds. These substances named hygrophorones possess a cyclopentenone skeleton. LC/ESI‐MS/MS presents a valuable tool for the identification of such compounds. The mass spectral behaviour of typical selected members of this group under positive and negative ion electrospray conditions is discussed. Using the ESI collision‐induced dissociation (CID) mass spectra of the [M + H] + and [M − H] − ions, respectively, the compounds can be classified with respect to the substitution pattern at the cyclopentenone ring and the type of oxygenation at C‐6 (hydroxy/acetoxy or oxo function) of the side chain. The elemental composition of the fragment ions was determined by ESI‐QqTOF measurements. Thus, in case of the negative ion CID mass spectra an unusual loss of CO 2 from the deprotonated molecular ions could be observed. Copyright © 2006 John Wiley & Sons, Ltd.