Development of a Stable Isotope Dilution LC–MS/MS Method for the <i>Alternaria</i> Toxins Tentoxin, Dihydrotentoxin, and Isotentoxin

Liu, Yang; Rychlik, Michael

doi:10.1021/jf305111w

Cited by 24 publications

(28 citation statements)

References 26 publications

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“…Notably, limited information was found about pyrenochaetic acid A (PyA), alternarienonic acid (AIA), and alloTeA and isoALT, recently reported in food samples for the first time [31,105] and metabolites such as AOH3S, AOH3G, AME3S, and AME3G [47,69]. In this way, AOH, AME, TeA, and TEN have been shown to occur in food samples frequently [82,97,108], while the occurrence of ALT, isoALT, ATX-I, and AAL toxins is of much lower incidence, mainly due to shortcomings in current analytical methodologies. Slight differences were observed based on the analyzed food matrices.…”

Section: Most Reported Mycotoxinsmentioning

confidence: 99%

AlternariaMycotoxins in Food and Feed: An Overview

Escrivá

Oueslati

Font

et al. 2017

Journal of Food Quality

140

127

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Alternaria is one of the major mycotoxigenic fungal genera with more than 70 reported metabolites. Alternaria mycotoxins showed notably toxicity, such as mutagenicity, carcinogenicity, induction of DNA strand break, sphingolipid metabolism disruption, or inhibition of enzymes activity and photophosphorylation. This review reports on the toxicity, stability, metabolism, current analytical methods, and prevalence of Alternaria mycotoxins in food and feed through the most recent published research. Half of the publications were focused on fruits, vegetables, and derived products-mainly tomato and apples-while cereals and cereal byproducts represented 38%. The most studied compounds were alternariol, alternariol methyl ether, tentoxin, and tenuazonic acid, but altenuene, altertoxins (I, II, and III), and macrosporin have been gaining importance in recent years. Solid-liquid extraction (50%) with acetonitrile or ethyl acetate was the most common extraction methodology, followed by QuEChERS and dilutiondirect injection (both 14%). High-and ultraperformance liquid chromatography coupled with tandem mass spectrometry was the predominant determination technique (80%). The highest levels of alternariol and alternariol methyl ether were found in lentils, oilseeds, tomatoes, carrots, juices, wines, and cereals. Tenuazonic acid highest levels were detected in cereals followed by beer, while alternariol, alternariol methyl ether, tenuazonic acid, and tentoxin were found in legumes, nuts, and oilseeds.

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Section: Most Reported Mycotoxinsmentioning

confidence: 99%

AlternariaMycotoxins in Food and Feed: An Overview

Escrivá

Oueslati

Font

et al. 2017

Journal of Food Quality

140

127

View full text Add to dashboard Cite

show abstract

“…Such a dilute-and-shoot approach has been chosen for this study as well. AOH, AME, TeA, and TEN have been shown to occur in food samples frequently (Liu and Rychlik 2013;Ackermann et al 2011;Lohrey et al 2013), while the occurrence of ALT, isoALT, ATX-I, and AAL toxins is of much lower incidence. The presence of AAL toxins has even not been reported in food samples up to date.…”

Section: Introductionmentioning

confidence: 99%

Survey of Alternaria toxin contamination in food from the German market, using a rapid HPLC-MS/MS approach

et al. 2015

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A HPLC-MS/MS-based method for the quantification of nine mycotoxins produced by fungi of the genus Alternaria in various food matrices was developed. The method relies on a single-step extraction, followed by dilution of the raw extract and direct analysis. In combination with an analysis time per sample of 12 min, the sample preparation is cost-effective and easy to handle. The method covers alternariol (AOH), alternariol monomethyl ether (AME), tenuazonic acid (TeA), altenuene (ALT), iso-altenuene (isoALT), tentoxin (TEN), altertoxin-I (ATX-I), and the AAL toxins TA1 and TA2. Some Alternaria toxins which are either not commercially available or very expensive, namely AOH, AME, ALT, isoALT, and ATX-I, were isolated as reference compounds from fungal cultures. The method was extensively validated for tomato products, bakery products, sunflower seeds, fruit juices, and vegetable oils. AOH, AME, TeA, and TEN were found in quantifiable amounts and 92.1% of all analyzed samples (n = 96) showed low level contamination with one or more Alternaria toxins. Based on the obtained results, the average daily exposure to Alternaria toxins in Germany was calculated.

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“…Tentoxin was fragmented into the deprotonated dipeptides [M − H] − Leu‐Me(Δ)Phe and [M − H] − Gly‐MeAla (Gly, glycine; Leu, leucine; MeAla, methylalanine; MePhe, methylphenylalanine) with m / z 271.2 and m / z 141.0, respectively (Liu and Rychlik, ). Hence, we used the MRM mode with ion transitions 413.3 → 271.2 and 413.3 → 141.0 in ESI − mode to analyse our sample.…”

Section: Resultsmentioning

confidence: 99%

“…To confirm the identity of the selected compound, we compared the retention time and fragmentation pattern with those of a (Liu and Rychlik, 2013). Hence, we used the MRM mode with ion transitions 413.3 → 271.2 and 413.3 → 141.0 in ESI − mode to analyse our sample.…”

Section: Confirmation Of Tentoxin Based On Uplc-ms/ms Analysismentioning

confidence: 99%

Comparative chemical screening and genetic analysis reveal tentoxin as a new virulence factor in Cochliobolus miyabeanus, the causal agent of brown spot disease on rice

Bruyne

Poucke

Mavungu

et al. 2015

Molecular Plant Pathology

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Brown spot disease, caused by Cochliobolus miyabeanus, is currently considered to be one of the most important yield reducers of rice (Oryza sativa L.). Despite its agricultural importance, little is known about the virulence mechanisms deployed by the fungus. Therefore, we set out to identify novel virulence factors with a role in disease development. This article reports, for the first time, the production of tentoxin by C. miyabeanus as a virulence factor during brown spot disease and the identification of the non-ribosomal protein synthetase (NRPS) CmNps3, responsible for tentoxin biosynthesis. We compared the chemical compounds produced by C. miyabeanus strains differing in virulence ability using ultra-high-performance liquid chromatography (UHPLC) coupled to high-resolution Orbitrap mass spectrometry (HRMS). The production of tentoxin by a highly virulent strain was revealed by principal component analysis of the detected ions and confirmed by UHPLC coupled to tandem-quadrupole mass spectrometry (MS/MS). The corresponding NRPS was identified by in silico genome analysis and confirmed by gene deletion. Infection tests with wild-type and Cmnps3 mutants showed that tentoxin acts as a virulence factor and is correlated with chlorosis development during the second phase of infection. Although rice has previously been classified as a tentoxin-insensitive plant species, our data demonstrate that tentoxin production by C. miyabeanus affects symptom development.

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Development of a Stable Isotope Dilution LC–MS/MS Method for the Alternaria Toxins Tentoxin, Dihydrotentoxin, and Isotentoxin

Cited by 24 publications

References 26 publications

AlternariaMycotoxins in Food and Feed: An Overview

AlternariaMycotoxins in Food and Feed: An Overview

Survey of Alternaria toxin contamination in food from the German market, using a rapid HPLC-MS/MS approach

Comparative chemical screening and genetic analysis reveal tentoxin as a new virulence factor in Cochliobolus miyabeanus, the causal agent of brown spot disease on rice

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