Stability of alternariol and alternariol monomethyl ether during food processing of tomato products

Estiarte, N.; Crespo-Sempere, A.; Marı́n, Sonia; Ramos, Ana M. González; Worobo, Randy W.

doi:10.1016/j.foodchem.2017.11.078

Cited by 31 publications

(19 citation statements)

References 16 publications

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“…Similarly, the loss of OTA, ZEA, AFB1, BEA, and ENNs in the products showed that thermal processing effectively decreased the content of these mycotoxins [ 52 , 56 , 57 ]. The 54% AOH reduction was reported for treatment at 110 °C for 20 min, whereas no significant effect was found for AME at the same temperature [ 58 ]. Based on Stadler et al [ 59 ], the parent mycotoxin can be structurally modified during food processing, including isomerization, decarboxylation, rearrangements, and the reaction with other small molecules [ 59 ].…”

Section: Introductionmentioning

confidence: 99%

Mycotoxins: Biotransformation and Bioavailability Assessment Using Caco-2 Cell Monolayer

Tran

Viktorová

Ruml

2020

Toxins

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The determination of mycotoxins content in food is not sufficient for the prediction of their potential in vivo cytotoxicity because it does not reflect their bioavailability and mutual interactions within complex matrices, which may significantly alter the toxic effects. Moreover, many mycotoxins undergo biotransformation and metabolization during the intestinal absorption process. Biotransformation is predominantly the conversion of mycotoxins meditated by cytochrome P450 and other enzymes. This should transform the toxins to nontoxic metabolites but it may possibly result in unexpectedly high toxicity. Therefore, the verification of biotransformation and bioavailability provides valuable information to correctly interpret occurrence data and biomonitoring results. Among all of the methods available, the in vitro models using monolayer formed by epithelial cells from the human colon (Caco-2 cell) have been extensively used for evaluating the permeability, bioavailability, intestinal transport, and metabolism of toxic and biologically active compounds. Here, the strengths and limitations of both in vivo and in vitro techniques used to determine bioavailability are reviewed, along with current detailed data about biotransformation of mycotoxins. Furthermore, the molecular mechanism of mycotoxin effects is also discussed regarding the disorder of intestinal barrier integrity induced by mycotoxins.

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Section: Introductionmentioning

confidence: 99%

Mycotoxins: Biotransformation and Bioavailability Assessment Using Caco-2 Cell Monolayer

Tran

Viktorová

Ruml

2020

Toxins

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“…Catechols formed by hydroxylation of AOH and AME may be further methylated by catechol-O-methyltransferase (Pfeiffer et al 2007;Tiessen et al 2017), while AME was also reported to be demethylated by microsomes of rat, human, and porcine liver (Pfeiffer et al 2007). However, AOH and AME are thermally and chemically rather stable in food matrices and therefore persistent during food processing (Estiarte et al 2018;Siegel et al 2010). Other dibenzopyrones are altenuene (ALT) and its isoform isoaltenuene (isoALT).…”

Section: Introductionmentioning

confidence: 99%

Bioavailability, metabolism, and excretion of a complex Alternaria culture extract versus altertoxin II: a comparative study in rats

et al. 2019

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Despite the frequent infection of agricultural crops by Alternaria spp., their toxic secondary metabolites and potential food contaminants lack comprehensive metabolic characterization. In this study, we investigated their bioavailability, metabolism, and excretion in vivo. A complex Alternaria culture extract (50 mg/kg body weight) containing 11 known toxins and the isolated lead toxin altertoxin II (0.7 mg/kg body weight) were administered per gavage to groups of 14 Sprague Dawley rats each. After 3 h and 24 h, plasma, urine and feces were collected to determine toxin recoveries. For reliable quantitation, an LC-MS/MS method for the simultaneous detection of 20 Alternaria toxins and metabolites was developed and optimized for either biological matrix. The obtained results demonstrated efficient excretion of alternariol (AOH) and its monomethyl ether (AME) via feces (> 89%) and urine (> 2.6%) after 24 h, while the majority of tenuazonic acid was recovered in urine (20 and 87% after 3 and 24 h, respectively). Moreover, modified forms of AOH and AME were identified in urine and fecal samples confirming both, mammalian phase-I (4-hydroxy-AOH) and phase-II (sulfates) biotransformation in vivo. Despite the comparably high doses, perylene quinones were recovered only at very low levels (altertoxin I, alterperylenol, < 0.06% in urine and plasma, < 5% in feces) or not at all (highly genotoxic, epoxide-holding altertoxin II, stemphyltoxin III). Interestingly, altertoxin I was detected in all matrices of rats receiving altertoxin II and suggests enzymatic de-epoxidation in vivo. In conclusion, the present study contributes valuable information to advance our understanding of the emerging Alternaria mycotoxins and their relevance on food safety.

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“…For the genotoxic AOH and AME, estimated exposure levels indicated a possible health concern (EFSA, 2011(EFSA, , 2016. These toxins were also shown to be chemically relatively stable during food processing (Estiarte et al, 2018;Siegel et al, 2010).…”

Section: Introductionmentioning

confidence: 99%

The fate of altertoxin II during tomato processing steps at a laboratory scale

Puntscher¹,

Marko²,

Warth³

2019

Preprint

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The emerging Alternaria mycotoxin altertoxin II demonstrated substantial genotoxicity in vitro. Ubiquitous Alternaria ssp. frequently infest various agricultural crops, leading to economic losses and also potential food safety issues caused by associated mycotoxin contaminations. Due to the lack of commercially available reference standards, data on the general chemical behavior, the occurrence and the biological/toxicological effects of altertoxin II are scarce. Since tomatoes are particularly prone to Alternaria infestations, we simulated the storage and food processing of intact tomatoes and purees after altertoxin II-addition. We observed significant decrease in altertoxin II concentrations during storage at room temperature and particularly under thermal stress, by employing a validated LC-MS/MS method. Moreover, the reduction to the compound’s epoxide group to the alcohol, i.e. the formation of altertoxin I, was determined at considerable ratios in intact tomato fruits suggesting effective enzymatic xenobiotic metabolism.

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Stability of alternariol and alternariol monomethyl ether during food processing of tomato products

Cited by 31 publications

References 16 publications

Mycotoxins: Biotransformation and Bioavailability Assessment Using Caco-2 Cell Monolayer

Mycotoxins: Biotransformation and Bioavailability Assessment Using Caco-2 Cell Monolayer

Bioavailability, metabolism, and excretion of a complex Alternaria culture extract versus altertoxin II: a comparative study in rats

The fate of altertoxin II during tomato processing steps at a laboratory scale

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