Development of analytical methods for the determination of tenuazonic acid analogues in food commodities

Asam, Stefan; Lichtenegger, Martina; Muzik, Kornelija; Liu, Yang; Frank, Oliver; Hofmann, Thomas; Rychlik, Michael

doi:10.1016/j.chroma.2013.03.015

Cited by 24 publications

(25 citation statements)

References 31 publications

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“…Also, TEA has poor MS properties (Siegel et al 2009 ; Asam et al 2011 ). Hence, LC-MS methods in the past either excluded TEA from Alternaria multi-toxin methods or focused only on TEA and its derivatisation with 2,4-dinitrophenylhydrazine (DNPH) (Lau et al 2003 ; Magnani et al 2007 ; Asam et al 2009 , 2013 ; Di Mavungu et al 2009 ; Siegel et al 2010 ). Recently, quantitative or semi-quantitative multi-compound methods including TEA and other Alternaria toxins were published despite the challenges as mentioned above (Prelle et al 2013 ; Varga et al 2013 ; Walravens et al 2014 ).…”

Section: Introductionmentioning

confidence: 99%

Simultaneous analysis ofAlternariatoxins and citrinin in tomato: an optimised method using liquid chromatography-tandem mass spectrometry

Tölgyesi

Stroka

Tamošiūnas

et al. 2015

Food Additives & Contaminants: Part A

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Alternaria toxins and citrinin are mycotoxins produced by fungi growing on different raw materials and agricultural commodities. Maximum levels of these toxins in foods are currently under consideration by the European Commission as a risk management measure. In this study, a new quantitative method is described for the determination of five Alternaria toxins and citrinin in tomato and tomato juice samples based on LC-MS/MS detection. Samples were extracted with pure methanol, followed by a derivatisation step with 2,4-dinitrophenylhydrazine to improve the determination of tenuazonic acid and to decrease the wide polarity difference between the compounds of interest. Samples were purified on hydrophilic-modified styrene polymer solid-phase extraction cartridges. High-performance liquid chromatographic columns packed with different core–shell materials were tested for the separation of toxins and a C-18 phase was in the final method applied to achieve sufficient separation of all relevant analytes. A key element of this approach was to prove successful transferability of the method to three different triple quadrupole mass spectrometers. A full single laboratory method validation was performed on two LC-MS/MS systems and performance characteristics met the predefined requirements. Moreover, the method was used in an international proficiency test and the satisfactory z-scores obtained (−0.1 to 0.8 in tomato juice samples) demonstrated the reliability of the approach described. The method will be validated in an inter-laboratory collaborative study and if the criteria for method precision are met, the method will be proposed as a new Work Item to the European Committee for Standardisation.

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Section: Introductionmentioning

confidence: 99%

Simultaneous analysis ofAlternariatoxins and citrinin in tomato: an optimised method using liquid chromatography-tandem mass spectrometry

Tölgyesi

Stroka

Tamošiūnas

et al. 2015

Food Additives & Contaminants: Part A

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“…Consequently, Alternaria mycotoxins were detected in cereals and derived products [46,[57][58][59][60][61][62][63][64][65][66][67][68][69][70][71][72][73][74][75][76], feed [74,[109][110][111][112][113], dairy products [114], grapes and by-products [27,77,115], tomatoes and derived products [31,47,77,81,106,113], nuts and by-products [102,116], spices [117], soybeans [76,116,118], sunflower seeds [85,104,107], vegetables [27,101], vegetable oils [105], strawberries …”

Section: Prevalence Of Alternaria 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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“…[24a] Due to fungal invasion on many plantsa nd vegetablec ommoditiest enuazonic acid (2)h as been found as natural contaminanti nf ood and feed and an umber of analytical methods to determine tenuazonic acid( 2)h ave been developed. [20,26] However,t he EFSA (European food safety authority) estimates the dietary exposure of 2 as harmless to human health. [24a] Over the last two decades, much interesth as been focused on the herbicidala ctivity of 2.…”

Section: Resultsmentioning

confidence: 99%

Aminotenuazonic Acid: Isolation, Structure Elucidation, Total Synthesis and Herbicidal Activity of a New Tetramic Acid from Fruiting Bodies of Laccaria Species

Schrey

Backenköhler

Kogler³

et al. 2019

Chemistry A European J

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5S,6S)-Aminotenuazonic acid, an ew 3-acyltetramic acid, related to the well-known mycotoxin tenuazonic acid has been isolated from fruiting bodies of Laccaria bicolor. Its structure was mostly established by analysiso fi ts 2D NMR and HR-(+ +)-ESI-MS spectra.Atotal synthesis starting from N-Boc-l-isoleucine gave (5S,6S)-aminotenuazonic acid in 8% yield over nine steps (67 % de). The key steps of the total synthesis are al ight-initiated Hofmann-Lçffler-Freytag radical chain reactiona nd aD ieckmann cyclisation.T he rela-tive and absolute configurations of the naturalp roduct were determined by comparison of its NMR and CD spectra with those of the corresponding enantiopure syntheticc ompounds. Metabolic profiling of crude extracts of different mushrooms showed that aminotenuazonic acid is present in all four of the investigated Laccaria species. Aminotenuazonic acid shows phytotoxic activities against the root and shoot growth of Lepidium sativum, Pinus sylvestris and Arabidopsis thaliana comparable to those of tenuazonic acid.

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Development of analytical methods for the determination of tenuazonic acid analogues in food commodities

Cited by 24 publications

References 31 publications

Simultaneous analysis ofAlternariatoxins and citrinin in tomato: an optimised method using liquid chromatography-tandem mass spectrometry

Simultaneous analysis ofAlternariatoxins and citrinin in tomato: an optimised method using liquid chromatography-tandem mass spectrometry

AlternariaMycotoxins in Food and Feed: An Overview

Aminotenuazonic Acid: Isolation, Structure Elucidation, Total Synthesis and Herbicidal Activity of a New Tetramic Acid from Fruiting Bodies of Laccaria Species

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