Structure Elucidation of New Fusarins Revealing Insights in the Rearrangement Mechanisms of the Fusarium Mycotoxin Fusarin C
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- 作者：Karin Kleigrewe ; Filiz Aydin ; Kirstin Hogrefe ; Patrick Piecuch ; Klaus Bergander ; Ernst-Ulrich W眉rthwein ; Hans-Ulrich Humpf
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2012
- 出版时间：May 30, 2012
- 年：2012
- 卷：60
- 期：21
- 页码：5497-5505
- 全文大小：395K
- 年卷期：v.60,no.21(May 30, 2012)
- ISSN：1520-5118
文摘
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.