ESI-MS and MS/MS identification of the first ceramide analogues of fumonisin B1 mycotoxin from a Fusarium verticillioides culture following RP-HPLC separation

T. Bartók, Á Szécsi, K. Juhász, M. Bartók, Á Mesterházy

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Following the earlier detection of six new esterified fumonisin B1 (EFB1) isomers containing three acyl groups in a Fusarium verticillioides-inoculated rice culture, it was assumed that linoleic, palmitic or oleic acid esterifies one of the free OH groups on the fumonisin backbone. On the basis of the results of our recent investigations we now propose that these EFB1 isomers are actually 3-O- and 5-O-acyl derivatives of FB1 (3-O-linoleoyl-FB1, 5-O-linoleoyl-FB1, 3-O-palmitoyl-FB1, 5-O-palmitoyl-FB1, 3-O-oleoyl-FB1 and 5-O-oleoyl-FB1). A F. verticillioides strain was identified that produced not only O-acyl-FB1 isomers, but also low amounts of three N-acyl derivatives (N-linoleoyl-FB1, N-palmitoyl-FB1 and N-oleoyl-FB1), which eluted from the HPLC column after the six O-acyl compounds and in the same sequence as for the O-acyl compounds. The characteristic positive and negative ESI-MS/MS spectra obtained after solid-phase extraction of the culture extract facilitated identification of these N-acyl-FB1 derivatives. The biosynthesis of N-palmitoyl-FB1 by F. verticillioides was verified by spiking the culture extract with synthetic N-palmitoyl-FB1. This is the first report of the separation and mass spectrometric identification of the six O-acyl- and three N-acyl-FB1 derivatives extracted from a F. verticillioides culture.

Original languageEnglish
Pages (from-to)1651-1659
Number of pages9
JournalFood Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment
Volume30
Issue number9
DOIs
Publication statusPublished - Sep 10 2013

Keywords

  • LC/MS
  • extraction
  • mycotoxins-fumonisins
  • rice culture

ASJC Scopus subject areas

  • Food Science
  • Chemistry(all)
  • Toxicology
  • Public Health, Environmental and Occupational Health
  • Health, Toxicology and Mutagenesis

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