Identification of the first fumonisin mycotoxins with three acyl groups by ESI-ITMS and ESI-TOFMS following RP-HPLC separation

Palmitoyl, linoleoyl and oleoyl EFB1 fumonisin isomers from a solid culture of Fusarium verticillioides

T. Bartók, L. Tölgyesi, Á Mesterházy, M. Bartók, Á Szécsi

Research output: Contribution to journalArticle

23 Citations (Scopus)

Abstract

The aim of this study was to apply RP-HPLC/ESI-ITMS and RP-HPLC/ESI-TOFMS to investigate and characterise six new higher molecular weight fumonisins (three pairs of isomers) extracted from a Fusarium verticillioides-infected solid rice culture. The ITMS and ITMS2 spectra clearly indicated the m/z values (960, 984 and 986) of the protonated molecules and the FB1 toxin-like structures of these compounds, respectively. Moreover, the data evaluation software of the TOFMS equipment unambiguously demonstrated the exact masses of the protonated molecules and the suggested empirical formulae (C50H89NO16, C52H89NO16 and C52H91NO16) of the new fumonisins, with mass accuracy in the range between 0.1 and -1.1 ppm. Subtraction of the empirical formula of FB1 toxin (C34H59NO15) from these formulae and correction for the mass of water split-off from the fumonisin molecule during ester formation resulted in the empirical formulae of the fumonisin backbone esterifying agents (fatty acids): C16H32O2 (palmitic acid, PA), C18H32O2 (linoleic acid, LA) and C18H32O2 (oleic acid, OA). We denoted the new compounds as esterified FB1 (EFB1) toxins, with the suggested names EFB1 PA, iso-EFB1 PA, EFB1 LA, iso-EFB1 LA, EFB1 OA and iso-EFB1 OA. The total amount of these new compounds comprised 0.1% of the FB1 concentration, which may be rated as significant when it is considered that these new components are significantly more apolar than earlier-described fumonisins, and their uptake into and toxicity elicited in the various tissues of living organisms may therefore also be significantly different from those of other fumonisins.

Original languageEnglish
Pages (from-to)1714-1723
Number of pages10
JournalFood Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment
Volume27
Issue number12
DOIs
Publication statusPublished - Dec 2010

Fingerprint

Fumonisins
Mycotoxins
fumonisins
Fusarium
Isomers
isomers
high performance liquid chromatography
High Pressure Liquid Chromatography
Palmitic Acid
Linoleic Acid
Oleic Acid
palmitic acid
oleic acid
linoleic acid
toxins
Molecules
Names
Toxicity
Fusarium verticillioides
Esters

Keywords

  • Cereals and grain
  • Extraction
  • Fumonisins
  • Liquid chromatography/mass spectrometry (lc/ms)

ASJC Scopus subject areas

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

Cite this

@article{d9a06c256c3842c281f05ad079ebb212,
title = "Identification of the first fumonisin mycotoxins with three acyl groups by ESI-ITMS and ESI-TOFMS following RP-HPLC separation: Palmitoyl, linoleoyl and oleoyl EFB1 fumonisin isomers from a solid culture of Fusarium verticillioides",
abstract = "The aim of this study was to apply RP-HPLC/ESI-ITMS and RP-HPLC/ESI-TOFMS to investigate and characterise six new higher molecular weight fumonisins (three pairs of isomers) extracted from a Fusarium verticillioides-infected solid rice culture. The ITMS and ITMS2 spectra clearly indicated the m/z values (960, 984 and 986) of the protonated molecules and the FB1 toxin-like structures of these compounds, respectively. Moreover, the data evaluation software of the TOFMS equipment unambiguously demonstrated the exact masses of the protonated molecules and the suggested empirical formulae (C50H89NO16, C52H89NO16 and C52H91NO16) of the new fumonisins, with mass accuracy in the range between 0.1 and -1.1 ppm. Subtraction of the empirical formula of FB1 toxin (C34H59NO15) from these formulae and correction for the mass of water split-off from the fumonisin molecule during ester formation resulted in the empirical formulae of the fumonisin backbone esterifying agents (fatty acids): C16H32O2 (palmitic acid, PA), C18H32O2 (linoleic acid, LA) and C18H32O2 (oleic acid, OA). We denoted the new compounds as esterified FB1 (EFB1) toxins, with the suggested names EFB1 PA, iso-EFB1 PA, EFB1 LA, iso-EFB1 LA, EFB1 OA and iso-EFB1 OA. The total amount of these new compounds comprised 0.1{\%} of the FB1 concentration, which may be rated as significant when it is considered that these new components are significantly more apolar than earlier-described fumonisins, and their uptake into and toxicity elicited in the various tissues of living organisms may therefore also be significantly different from those of other fumonisins.",
keywords = "Cereals and grain, Extraction, Fumonisins, Liquid chromatography/mass spectrometry (lc/ms)",
author = "T. Bart{\'o}k and L. T{\"o}lgyesi and {\'A} Mesterh{\'a}zy and M. Bart{\'o}k and {\'A} Sz{\'e}csi",
year = "2010",
month = "12",
doi = "10.1080/19440049.2010.521958",
language = "English",
volume = "27",
pages = "1714--1723",
journal = "Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment",
issn = "1944-0049",
publisher = "Taylor and Francis Ltd.",
number = "12",

}

TY - JOUR

T1 - Identification of the first fumonisin mycotoxins with three acyl groups by ESI-ITMS and ESI-TOFMS following RP-HPLC separation

T2 - Palmitoyl, linoleoyl and oleoyl EFB1 fumonisin isomers from a solid culture of Fusarium verticillioides

AU - Bartók, T.

AU - Tölgyesi, L.

AU - Mesterházy, Á

AU - Bartók, M.

AU - Szécsi, Á

PY - 2010/12

Y1 - 2010/12

N2 - The aim of this study was to apply RP-HPLC/ESI-ITMS and RP-HPLC/ESI-TOFMS to investigate and characterise six new higher molecular weight fumonisins (three pairs of isomers) extracted from a Fusarium verticillioides-infected solid rice culture. The ITMS and ITMS2 spectra clearly indicated the m/z values (960, 984 and 986) of the protonated molecules and the FB1 toxin-like structures of these compounds, respectively. Moreover, the data evaluation software of the TOFMS equipment unambiguously demonstrated the exact masses of the protonated molecules and the suggested empirical formulae (C50H89NO16, C52H89NO16 and C52H91NO16) of the new fumonisins, with mass accuracy in the range between 0.1 and -1.1 ppm. Subtraction of the empirical formula of FB1 toxin (C34H59NO15) from these formulae and correction for the mass of water split-off from the fumonisin molecule during ester formation resulted in the empirical formulae of the fumonisin backbone esterifying agents (fatty acids): C16H32O2 (palmitic acid, PA), C18H32O2 (linoleic acid, LA) and C18H32O2 (oleic acid, OA). We denoted the new compounds as esterified FB1 (EFB1) toxins, with the suggested names EFB1 PA, iso-EFB1 PA, EFB1 LA, iso-EFB1 LA, EFB1 OA and iso-EFB1 OA. The total amount of these new compounds comprised 0.1% of the FB1 concentration, which may be rated as significant when it is considered that these new components are significantly more apolar than earlier-described fumonisins, and their uptake into and toxicity elicited in the various tissues of living organisms may therefore also be significantly different from those of other fumonisins.

AB - The aim of this study was to apply RP-HPLC/ESI-ITMS and RP-HPLC/ESI-TOFMS to investigate and characterise six new higher molecular weight fumonisins (three pairs of isomers) extracted from a Fusarium verticillioides-infected solid rice culture. The ITMS and ITMS2 spectra clearly indicated the m/z values (960, 984 and 986) of the protonated molecules and the FB1 toxin-like structures of these compounds, respectively. Moreover, the data evaluation software of the TOFMS equipment unambiguously demonstrated the exact masses of the protonated molecules and the suggested empirical formulae (C50H89NO16, C52H89NO16 and C52H91NO16) of the new fumonisins, with mass accuracy in the range between 0.1 and -1.1 ppm. Subtraction of the empirical formula of FB1 toxin (C34H59NO15) from these formulae and correction for the mass of water split-off from the fumonisin molecule during ester formation resulted in the empirical formulae of the fumonisin backbone esterifying agents (fatty acids): C16H32O2 (palmitic acid, PA), C18H32O2 (linoleic acid, LA) and C18H32O2 (oleic acid, OA). We denoted the new compounds as esterified FB1 (EFB1) toxins, with the suggested names EFB1 PA, iso-EFB1 PA, EFB1 LA, iso-EFB1 LA, EFB1 OA and iso-EFB1 OA. The total amount of these new compounds comprised 0.1% of the FB1 concentration, which may be rated as significant when it is considered that these new components are significantly more apolar than earlier-described fumonisins, and their uptake into and toxicity elicited in the various tissues of living organisms may therefore also be significantly different from those of other fumonisins.

KW - Cereals and grain

KW - Extraction

KW - Fumonisins

KW - Liquid chromatography/mass spectrometry (lc/ms)

UR - http://www.scopus.com/inward/record.url?scp=78649714026&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=78649714026&partnerID=8YFLogxK

U2 - 10.1080/19440049.2010.521958

DO - 10.1080/19440049.2010.521958

M3 - Article

VL - 27

SP - 1714

EP - 1723

JO - Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment

JF - Food Additives and Contaminants - Part A Chemistry, Analysis, Control, Exposure and Risk Assessment

SN - 1944-0049

IS - 12

ER -