Sterigmatocystin (STC) is a mycotoxin produced by fungi of many different Aspergillus species. Other species such as Bipolaris, Chaetomium, Emiricella are also able to produce STC. STC producing fungi were frequently isolated from different foodstuffs, while STC was regularly detected in grains, corn, bread, cheese, spices, coffee beans, soybeans, pistachio nuts, animal feed and silage. STC shows different toxicological, mutagenic and carcinogenic effects in animals and has been recognized as a 2B carcinogen (possible human carcinogen) by International Agency for Research on Cancer. There are more than 775 publications available in Scopus (and more than 505 in PubMed) mentioning STC, but there is no summary information available about STC occurrence and analysis in food. This review presents an overview of the worldwide information on the occurrence of STC in different foodstuffs during the last 40 years, and describes the progress made in analytical methodology for the determination of STC in food.
In vivo metabolism of masked or conjugated mycotoxins is poorly documented as standards are not commercially available and indirect analysis using hydrolytic enzymes is difficult to validate and cumbersome. We synthesised zearalenone-14-glucoside (ZEA-14G) chemically. Deoxynivalenol-3-glucuronide (DON-3GlcA) and glucuronides of 3- and 15-acetyl-deoxynivalenol (3-and 15-ADON-GlcAs), de-epoxydeoxynivalenol, zearalenone (ZEA), alpha- and beta-zearalenol (alpha- and beta-ZOL) were synthesised using rat microsomes. For the first time three ADON-GlcAs were synthesised: two 3-ADON-GlcAs and one 15-ADON-GlcA. After purification, the masked mycotoxin and the metabolites were characterised by NMR (DON-3GlcA, ZEA-14G) or by full scan MS, MS/MS fragmentation, UV-spectra, beta-glucosidase and beta-glucuronidase treatment. In a first experiment, rats were fed orally DON-3-glucoside (DON-3G) and ZEA-14G, together with C-13-DON and C-13-ZEA and were sacrificed after 55 minutes. A total of 21 masked metabolites, metabolites and parent mycotoxins were quantified in rat organs. Whereas DON-3G was hardly hydrolysed in the stomach, ZEA was clearly formed from ZEA-14G. In a second experiment, 3-and 15-ADON were given orally to rats. The acetylated forms of DON were hydrolysed in the stomach, in contrast to DON-3G. Rats can directly glucuronidate ADONs without deacetylation. Neither DOM, alpha-or beta-ZOL nor their glucuronides could be quantified. Glucuronidated 3-ADON accumulated in the small intestines, together with DON-3GlcA in rats fed orally with 3- and 15-ADON. These differences in masked mycotoxins metabolism can be important in risk analysis of masked mycotoxins in food and feed
Seven commercially available deoxynivalenol (DON) and zearalenone (ZEN) immunoaffinity columns (IACs) were tested for cross-reactivity to conjugated forms (3-acetyl-deoxynivalenol, 15-acetyl-deoxynivalenol, DON-3-glucoside, DON-3-glucuronide, ZEN-glucosides, ZEN-glucuronide) and metabolites (de-epoxydeoxynivalenol, α-zearalenol, β-zearalenol) and nivalenol (NIV), using a semi-quantitative multi-mycotoxin ultra-performance liquid chromatography-tandem mass spectrometry method. The DON IACs showed cross-reactivity for nearly all DON derivatives tested. The ZEN IACs showed limited cross-reactivity to some of the ZEN derivatives. The IACs were evaluated for their potential use as sample clean-up for mycotoxins in serum.
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