Sulfation of β-resorcylic acid esters—first synthesis of zearalenone-14-sulfate

Mikula, Hannes; Sohr, Barbara; Skrinjar, Philipp; Wéber, Júlia; Hametner, Christian; Berthiller, Franz; Krska, Rudolf; Adam, Gerhard; Fröhlich, Johannes

doi:10.1016/j.tetlet.2013.04.059

Cited by 17 publications

(18 citation statements)

References 35 publications

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“…This has led to the identification and/or production of DON3G, T2-G and ZEN14G. Also ZEN14S has been produced by chemical synthesis (Mikula et al, 2013a), by isolation from Fusarium inoculated rice (De Boevre et al, 2012;Plasencia and Mirocha, 1991) and through microbial transformation (Rhizopus arrhizus) (el-Sharkaway et al, 1991). Synthesis still remains a major hurdle for toxicokinetic and toxicity research, as animal trials and toxicity tests often require large amounts of toxins.…”

Section: Conclusion and Future Perspectivesmentioning

confidence: 99%

Modified Fusarium mycotoxins unmasked: From occurrence in cereals to animal and human excretion

Broekaert

Devreese

Baere

et al. 2015

Food and Chemical Toxicology

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Section: Conclusion and Future Perspectivesmentioning

confidence: 99%

Modified Fusarium mycotoxins unmasked: From occurrence in cereals to animal and human excretion

Broekaert

Devreese

Baere

et al. 2015

Food and Chemical Toxicology

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“…[18] Compounds were analyzed with 1 H and 13 C NMR spectroscopic methods using a fully automated Bruker Avance-III 400MHz NMR spectrometer. The final product was confirmed with low-resolution electrospray ionization (LRMS (ESI negative mode)) mass spectroscopy analysis recorded on a Bruker 9.4 T Apex-Qh hybrid Fourier transfer ion-cyclotron resonance (FT-ICR) instrument.…”

Section: Methodsmentioning

confidence: 99%

“…[18] The final compound was obtained first through esterification of salicylic acid to produce methyl salicylate 2 . We then used chlorosulfuric acid 2,2,2-trichloroethyl ester as the sulfation reagent, and in the last step deprotection of the TCE sulfate led to conversion of the desired product.…”

mentioning

confidence: 99%

A CatalyCEST MRI Contrast Agent that Can Simultaneously Detect Two Enzyme Activities

2016

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The simultaneous detection of multiple enzyme activities can improve the specificity of disease diagnoses. We have synthesized and characterized a diamagnetic CEST MRI contrast agent that can simultaneously detect two enzyme activities. Sulfatase and esterase enzymes cleaved the ligands of the CEST agent, to release salicylic acid that was detected with CEST MRI. Importantly, both enzymes were required to activate the agent to produce a CEST MRI contrast, and the CEST agent was stable without enzyme treatment. These results have established that this diamagnetic CEST MRI contrast agent is a platform technology with a modular design that can be potentially exploited to detect other combinations of enzyme activities, which can expand the armamentarium of contrast agents for molecular imaging.

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“…The chemical synthesis of the ammonium salt of ZEN14Sulf was first accomplished by Mikula et al. (). In a more recent paper, the same laboratory reported on the chemical synthesis of ZEN16Sulf (Mikula et al., ).…”

Section: Chemistrymentioning

confidence: 99%

Appropriateness to set a group health‐based guidance value for zearalenone and its modified forms

Hoogenboom¹

2016

EFS2

101

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The current tolerable daily intake (TDI) for zearalenone (ZEN) of 0.25 lg/kg body weight (bw) per day established by the EFSA Panel for Contaminants in the Food Chain (CONTAM Panel) in 2011 is based on oestrogenicity in pigs. No new studies were identified to change this TDI. The modified forms of ZEN identified are phase I and phase II metabolites. Phase I metabolites are mainly formed through reduction. Phase II metabolites are formed by conjugation of ZEN and its phase I metabolites with glucose or sulfate, and in animals glucuronic acid. The few data on the occurrence of modified forms of ZEN indicated that cereal-based foods are the main source, containing amounts varying from a few up to 100% of ZEN. Most of the phase I metabolites have oestrogenic activity and it is assumed that their combined action will be additive. The CONTAM Panel found it appropriate to set a group TDI of 0.25 lg/kg bw per day expressed as ZEN equivalents for ZEN and its modified forms (phase I and phase II metabolites). To account for differences in in vivo oestrogenic potency, each phase I metabolite was assigned a potency factor relative to ZEN to be applied to exposure estimates of the respective ZEN metabolites. It was assumed that conjugates (phase II metabolites) of ZEN and its phase I metabolites, which per se have no oestrogenic activity, will be cleaved releasing ZEN and its phase I metabolites. These conjugates were assigned the same relative potency factors as their aglycones. The overall uncertainty associated with the present assessment is considered as high. It would rather overestimate than underestimate any risk of modified ZEN. Several aspects of the uncertainty could be reduced provided more data are made available on oestrogenicity of modified ZEN, in particular a-zearalenol, in pigs.

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Sulfation of β-resorcylic acid esters—first synthesis of zearalenone-14-sulfate

Cited by 17 publications

References 35 publications

Modified Fusarium mycotoxins unmasked: From occurrence in cereals to animal and human excretion

Modified Fusarium mycotoxins unmasked: From occurrence in cereals to animal and human excretion

A CatalyCEST MRI Contrast Agent that Can Simultaneously Detect Two Enzyme Activities

Appropriateness to set a group health‐based guidance value for zearalenone and its modified forms

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