Simultaneous determination of the trans and cis forms of zearalenone in cereal products by high-performance liquid chromatography with voltammetric detection

Smyth, Malcolm R.; Frischkorn, C. G. B.

doi:10.1016/s0003-2670(01)93168-x

Cited by 26 publications

(5 citation statements)

References 2 publications

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“…Cis-ZEN was reported to occur in cereal products (Smyth and Frischkorn, 1980), edible oils and wet maize meal when exposed to UV-light K€ oppen et al, 2012b). The practical relevance of these findings needs to be clarified by screening feedstuffs for the natural occurrence of cis-ZEN.…”

Section: Occurrence In Feedmentioning

confidence: 99%

Invited review: Diagnosis of zearalenone (ZEN) exposure of farm animals and transfer of its residues into edible tissues (carry over)

Dänicke

Winkler

2015

Food and Chemical Toxicology

103

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Section: Occurrence In Feedmentioning

confidence: 99%

Invited review: Diagnosis of zearalenone (ZEN) exposure of farm animals and transfer of its residues into edible tissues (carry over)

Dänicke

Winkler

2015

Food and Chemical Toxicology

103

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“…Routes of entry into the food chain might arise from the production of cis -ZEN by fungi , or upon exposure of trans -ZEN contaminated foods to (UV-) light, although the detection of cis -ZEN in fungi cultures might be a consequence of exposure to daylight, as biosynthetic pathways are generally stereoselective. To date, cis -ZEN has been detected in different commodities like ground maize, sugar beets, and edible oils as well as in wet ground maize intended for animal feeding. − …”

Section: Introductionmentioning

confidence: 99%

In Vitro Phase I Metabolism of cis-Zearalenone

Drzymala

Herrmann

Maul

et al. 2014

Chem. Res. Toxicol.

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The present study investigates the in vitro phase I metabolism of cis-zearalenone (cis-ZEN) in rat liver microsomes and human liver microsomes. cis-ZEN is an often ignored isomer of the trans-configured Fusarium mycotoxin zearalenone (trans-ZEN). Upon the influence of (UV-) light, trans-ZEN isomerizes to cis-ZEN. Therefore, cis-ZEN is also present in food and feed. The aim of our study was to evaluate the in vitro phase I metabolism of cis-ZEN in comparison to that of trans-ZEN. As a result, an extensive metabolization of cis-ZEN is observed for rat and human liver microsomes as analyzed by HPLC-MS/MS and high-resolution MS. Kinetic investigations based on the substrate depletion approach showed no significant difference in rate constants and half-lives for cis- and trans-ZEN in rat microsomes. In contrast, cis-ZEN was depleted about 1.4-fold faster than trans-ZEN in human microsomes. The metabolite pattern of cis-ZEN revealed a total of 10 phase I metabolites. Its reduction products, α- and β-cis-zearalenol (α- and β-cis-ZEL), were found as metabolites in both species, with α-cis-ZEL being a major metabolite in rat liver microsomes. Both compounds were identified by co-chromatography with synthesized authentic standards. A further major metabolite in rat microsomes was monohydroxylated cis-ZEN. In human microsomes, monohydroxylated cis-ZEN is the single dominant peak of the metabolite profile. Our study discloses three metabolic pathways for cis-ZEN: reduction of the keto-group, monohydroxylation, and a combination of both. Because these routes have been reported for trans-ZEN, we conclude that the phase I metabolism of cis-ZEN is essentially similar to that of its trans isomer. As trans-ZEN is prone to metabolic activation, leading to the formation of more estrogenic metabolites, the novel metabolites of cis-ZEN reported in this study, in particular α-cis-ZEL, might also show higher estrogenicity.

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“…Because only little is known about the occurrence, fate, and risks associated with cis-zearalenone entering the food chain, a major problem could arise for the official control of foodstuffs and consumer protection. 21 Most of the various analytical methods for the determination of zearalenone in food and feed, based on HPLC coupled to fluorescence or mass spectrometric detection, 22−24 were not developed and optimized to distinguish between trans-and cis-zearalenone. The separation and reliable quantitation of one or both zearalenone isomers strongly depends on the chromatographic conditions, posing a risk of noncomparable results and, consequently, leading to consumer health risks and economic problems.…”

Section: ■ Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photochemical trans-/cis-Isomerization and Quantitation of Zearalenone in Edible Oils

Köppen

Riedel

Proske

et al. 2012

J. Agric. Food Chem.

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The emphasis of the present work was to investigate the photochemical conversion of trans- to cis-zearalenone in edible oils under real-life conditions. For quantitation purposes a cis-zearalenone standard was synthesized and characterized for its identity and purity (≥95%) by (1)H NMR, X-ray crystallography, HPLC fluorescence and mass spectrometric detection. In a sample survey of 12 edible oils (9 corn oils, 3 hempseed oils) from local supermarkets all corn oils contained trans-zearalenone (median 194 μg/kg), but no cis-zearalenone was detected. For alteration studies trans-zearalenone contaminated corn oils were exposed to sunlight over 4 and 30 weeks, revealing an obvious shift toward cis-zearalenone up to a cis/trans ratio of 9:1 by storage in colorless glass bottles. Irradiation experiments of trans-zearalenone in different organic solvents confirmed the preferred formation of cis-zearalenone possibly caused by entropic effects rather than by enthalpic entities as investigated by quantum chemical and classical force field simulations.

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Simultaneous determination of the trans and cis forms of zearalenone in cereal products by high-performance liquid chromatography with voltammetric detection

Cited by 26 publications

References 2 publications

Invited review: Diagnosis of zearalenone (ZEN) exposure of farm animals and transfer of its residues into edible tissues (carry over)

Invited review: Diagnosis of zearalenone (ZEN) exposure of farm animals and transfer of its residues into edible tissues (carry over)

In Vitro Phase I Metabolism of cis-Zearalenone

Photochemical trans-/cis-Isomerization and Quantitation of Zearalenone in Edible Oils

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