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Gewählte Publikation:

Berthiller, F., Hametner, C., Krenn, P., Schweiger, W., Ludwig, R., Adam, G., Krska, R., Schuhmacher, R..
(2009): Preparation and characterization of the masked Fusarium mycotoxins zearalenone-4O-beta-D-glucopyranoside, alpha-zearalenol-4O-beta-D-glucopyranoside and beta-zearalenol-4O-beta-D-glucopyranoside by MS/MS and 2D-NMR
FOOD ADDIT CONTAM, 26, 207-213; ISSN 0265-203X FullText FullText_BOKU

Glucosides of several Fusarium mycotoxins occur in naturally infected cereals and may contribute to an increased content to the total mycotoxin load of food and feed. The paper presents the results of a fermentation procedure to produce zearalenone-4O-beta-D-glucopyranoside from zearalenone using an engineered Saccharomyces cerevisiae strain, expressing the Arabidopsis thaliana UDP-glucosyltransferase UGT73C6. About 24 mg of zearalenone-4O-beta-D-glucopyranoside was obtained from 50 mg of zearalenone and further purified. A total of 10 mg of the glucoside were reduced with sodium borohydride, yielding 4.1 mg alpha-zearalenol-4O-beta-D-glucopyranoside and 4.5 mg beta-zearalenol-4O-beta-D-glucopyranoside at purities higher than 99%. To confirm the identities of the three produced glucosides, MS and MS/MS spectra were acquired using negative electrospray ionization. Besides the deprotonated ions at m/z 479 or 481, respectively, in full-scan mode, fragments, adducts, and dimers were recorded and assigned. MS/MS spectra of the glucosylated substances yielded the deprotonated ions of the mycotoxins zearalenone, alpha-zearalenol, beta-zearalenol and their fragments, respectively. Unambiguous structural assignment of the three substances was achieved using two-dimensional NMR methods. This way, the glucose attachment to position C-4, the beta-configuration of the sugar unit and the stereo-chemical assignment of the zearalenol hydroxyl group at C-6' were proven.
Autor*innen der BOKU Wien:
Adam Gerhard
Berthiller Franz
Krska Rudolf
Ludwig Roland
Schuhmacher Rainer
Schweiger Wolfgang
Find related publications in this database (using NML MeSH Indexing)
Animal Feed -
Animals -
Fermentation -
Fusarium - chemistry
Glucosides - chemical synthesis
Humans -
Magnetic Resonance Spectroscopy - methods
Mycotoxins - analogs & derivatives
Saccharomyces - chemistry
Swine -
Zeranol - analogs & derivatives

Find related publications in this database (Keywords)
mass spectrometry
nuclear magnetic resonance

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