title: Structure elucidation of new fusarins revealing insights in the rearrangement mechanisms of the Fusarium mycotoxin fusarin C.
abstract: Fusarin C is a Fusarium mycotoxin that rearranges under reversed phase chromatographic conditions. In this study, the rearrangement of fusarin C was examined in detail, and the formation of fusarins under different conditions was optimized. All relevant fusarins including (10Z)-, (8Z)-, and (6Z)-fusarin C were isolated and identified by NMR. To confirm the involvement of the 2-pyrrolidone ring in the rearrangement of fusarin C, 15-methoxy-fusarin C was synthesized. For the first time, the structure of open-chain fusarin C was elucidated, and on the basis of these data, the rearrangement product of fusarin C was identified as epi-fusarin C. The results were confirmed by detailed NMR measurements and density functional theory calculations. Furthermore, a new fusarin C like metabolite, which was named dihydrofusarin C, was detected by analysis of the crude extract of fusarin C with high-performance liquid chromatography coupled to UV and Fourier transform mass spectrometry.
authors.affiliation: Institute of Food Chemistry, Westfälische Wilhelms-Universität Münster, Münster, Germany.
authors.forename: Karin
authors.initials: K
authors.lastname: Kleigrewe
authors.forename: Filiz
authors.initials: F
authors.lastname: Aydin
authors.forename: Kirstin
authors.initials: K
authors.lastname: Hogrefe
authors.forename: Patrick
authors.initials: P
authors.lastname: Piecuch
authors.forename: Klaus
authors.initials: K
authors.lastname: Bergander
authors.forename: Ernst-Ulrich
authors.initials: EU
authors.lastname: Würthwein
authors.forename: Hans-Ulrich
authors.initials: HU
authors.lastname: Humpf
mesh_terms: D005670:Fusarium / Q000737:chemistry* / Q000378:metabolism; D015394:Molecular Structure; D009183:Mycotoxins / Q000737:chemistry* / Q000378:metabolism; D011090:Polyenes / Q000737:chemistry* / Q000378:metabolism
chemical_list: D009183:Mycotoxins; D011090:Polyenes; C041403:fusarin C