Zearalenone-16- o -glucoside: A new masked mycotoxin

Maria Paula Kovalsky Paris, Wolfgang Schweiger, Christian Hametner, Romana Stückler, Gary J. Muehlbauer, Elisabeth Varga, Rudolf Krska, Franz Berthiller, Gerhard Adam

Research output: Contribution to journalArticlepeer-review

54 Scopus citations

Abstract

This paper reports the identification of a barley UDP-glucosyltransferase, HvUGT14077, which is able to convert the estrogenic Fusarium mycotoxin zearalenone into a near-equimolar mixture of the known masked mycotoxin zearalenone-14-O-β-glucoside and a new glucose conjugate, zearalenone-16-O-β-glucoside. Biocatalytical production using engineered yeast expressing the HvUGT14077 gene allowed structural elucidation of this compound. The purified zearalenone-16-O-β-glucoside was used as an analytical calibrant in zearalenone metabolization experiments. This study confirmed the formation of this new masked mycotoxin in barley seedlings as well as in wheat and Brachypodium distachyon cell suspension cultures. In barley roots, up to 18-fold higher levels of zearalenone-16-O-β-glucoside compared to the known zearalenone-14-O-β-glucoside were found. Incubation of zearalenone-16-O-β-glucoside with human fecal slurry showed that this conjugate can also be hydrolyzed rapidly by intestinal bacteria, converting the glucoside back to the parental mycotoxin. Consequently, it should be considered as an additional masked form of zearalenone with potential relevance for food safety.

Original languageEnglish (US)
Pages (from-to)1181-1189
Number of pages9
JournalJournal of agricultural and food chemistry
Volume62
Issue number5
DOIs
StatePublished - Feb 5 2014

Keywords

  • Brachypodium
  • Fusarium
  • UDP-glucosyltransferase
  • barley
  • heterologous expression
  • wheat
  • xenoestrogen
  • yeast
  • zearalenone

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