title: Negative ion tandem mass spectrometry of prenylated fungal metabolites and their derivatives.
abstract: Liquid chromatography negative ion electrospray ionisation tandem mass spectrometry has been used for characterisation of naturally occurring prenylated fungal metabolites and synthetic derivatives. The fragmentation studies allow an elucidation of the decomposition pathways for these compounds. It could be shown, that the prenyl side chain is degraded by successive radical losses of C(5) units. Both the benzoquinones and the phenolic derivatives display significant key ions comprising the aromatic ring. In some cases, the formation of significant oxygen-free key ions could be evidenced by high-resolution MS/MS measurements. Furthermore, the different types of basic skeletons, benzoquinones and phenol type as well as cyclic prenylated compounds, can be differentiated by their MS/MS behaviour. Figure Fruiting bodies of Suillus bovinus, the structure of boviquinone-4 and its negative ion MS2 spectrum.
authors.affiliation: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, 06120 Halle, Germany.
authors.forename: Ramona
authors.initials: R
authors.lastname: Heinke
authors.forename: Norbert
authors.initials: N
authors.lastname: Arnold
authors.forename: Ludger
authors.initials: L
authors.lastname: Wessjohann
authors.forename: Jürgen
authors.initials: J
authors.lastname: Schmidt
mesh_terms: D001487:Basidiomycota / Q000378:metabolism; D016227:Benzoquinones / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D005658:Fungi / Q000378:metabolism*; D007477:Ions; D013058:Mass Spectrometry / Q000379:methods; D008956:Models, Chemical; D009930:Organic Chemicals / Q000737:chemistry; D019800:Phenol / Q000737:chemistry; D010636:Phenols / Q000737:chemistry; D054876:Prenylation; D011809:Quinones / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*; D053719:Tandem Mass Spectrometry / Q000379:methods*
chemical_list: D016227:Benzoquinones; D007477:Ions; D009930:Organic Chemicals; D010636:Phenols; D011809:Quinones; D019800:Phenol; C004532:quinone; D002244:Carbon