The mycotoxins diacetoxyscirpenol, deoxynivalenol, and zearalenone, produced by Fusarium roseum, were found naturally occurring in mixed feed samples. In all cases analyzed, deoxynivalenol occurred together with zearalenone. The natural occurrence of zearalenone in sesame seed is reported for the first time. Strains of F. roseum isolated in various parts of the world from feed implicated in animal mycotoxicosis produced monoacetoxyscirpenol, diacetoxyscirpenol, deoxynivalenol, and zearalenone.
One diastereomer of trans-zearalenol [2,4-dihydroxy-6-(6,10-dihydroxy-trans-1-undecenyl)-benzoic acid-y-lactone] was isolated from cultures of Fusarium roseum 'Gibbosum.' This strongly estrogenic metabolite was identified by analysis of its mass spectrum and its behavior in thin-layer, high-pressure liquid and gasliquid chromatographic systems. The concentration of zearalenol in cultures was 563 ,ug/g, or 7% of the 8,000-,ug/g zearalenone content, while the two diastereomers
Tritium-labeled T-2 toxin [4~,15-diacetoxy,8a-(3-methylbutyryloxy)-3a-hydroxy-12,13-epoxytrichothec-g-ene] was synthesized using a two-step process. First, the C-3 hydroxyl was oxidized to a ketone using either chromium trioxide-pyridine or dimethyl sulfide-N-chlorosuccinimide complex. In step two, the ketone was reduced with either tritiated sodium cyanoborohydride or tritiated sodium borohydride to a mixture of epimers which were separable by thin-layer chromatography. The a epimer (naturally occurring T-2 toxin) was formed predominantly, i.e., a to ratio was 4 to 1. Final reduction with tritiated sodium borohydride yielded [3-3H]T-2 toxin in 23% yield with a specific activity of 790 mCi/mmol. The labeled product, when equilibrated with 0.01 N HC1, did not lose the tritium, indicating that no labile tritium was incorporated into T-2 toxin. Further, the oxidation of [3-3H]T-2 toxin resulted in total loss of activity in the corresponding ketone.The metabolites of species of Fusarium are commonly found in foodstuff and are prominent because of their association with cases of mycotoxicoses of humans and animals. One such metabolite, T-2 toxin (1) [4&15-diacetoxy,8a-( 3-methylbutyryloxy)-3a-hydroxy-12,13-epoxytrichothec-g-ene] has been implicated as a mycotoxin responsible for the hemorrhagic syndrome and death of dairy cattle (Hsu et al., 1972). T-2 toxin causes an extreme dermal necrosis in most animals and is also one of the most
A versatile method for the detection of zearalenone is described, employing options of either thin layer chromatography (TLC), gas-liquid chromatography (GLC), ultraviolet chromatography, GLC-mass spectrometry, or combinations of all of these. Zearalenone is extracted with either a Soxhlet apparatus or the more rapid and convenient batch extraction technique with equal efficiency. Cleanup of the extract involves either a base (NaOH) treatment and partition with water or an acetonitrile- petroleum ether partition. A chloroformethanol (97+3) solvent system is used for analysis by TLC with confirmation by fluorescent properties. The limit of detection on the TLC plate is 0.1 μg, while the sensitivity for the TLC method is about 50 ppb. Best quantitative results are obtained by analytical procedures involving GLC. The limit of sensitivity by GLC is less than 50 ppb. The derivatives dimethoxyzearalenone and methyl oxime-di- TMS-ether-zearalenone are prepared to confirm the presence of zearalenone. Zearalenone can also be analyzed both qualitatively and quantitatively by ultraviolet spectrophotometry. For quantitation, a standard curve is constructed of the absorption at 274 nm. The limit of detection is between 0.1 and 0.5 μg/ml. Analysis by combination GLC and mass spectroscopy is also described along with analysis by multiple ion detection. Per cent recovery is 83.5±7. The method described is suitable for analysis of the concentrations of zearalenone normally encountered in nature and thought to be significant.
The trichothecene toxins are a chemical group of fungal metabolites characterized by a tetracyclic 12, 13‐epoxy‐trichothec‐9‐ene skeleton. There are over 40 naturally occurring derivatives produced predominantly by species ofFusarium but also produced by species ofCephalosporium, Myrothecium, Trichoderma, andStachybotrys. The trichothecene derivatives most commonly encountered in feedstuff are: T‐2 toxin, diacetoxyscirpenol (DAS), deoxynivalenol (vomitoxin) and nivalenol. Deoxynivalenol has been isolated from corn and mixed feed more frequently than the other derivatives reported, and moreover, it is frequently found together with the fungal estrogen zearalenone. Deoxynivalenol has frequently been associated with corn refused by swine, vomiting in dogs, and corn used by humans in South Africa. Deoxynivalenol is produced byFusarium roseum, an organism that is commonly found infecting corn in the field and corn stored on‐the‐cob in cribs in the Midwest. The trichothecenes have been implicated in diseases of man called alimentary toxic aleukia in the USSR and have been found in corn in the Transkei where the incidence of esophageal cancer is high. Among domestic animals, trichothecenes such as T‐2 toxin, DAS and deoxynivalenol have been implicated in diseases characterized by a hemorrhagic syndrome in cows and swine, vomiting in swine and dogs, decrease in avian egg production and body weight, refusal of feed by swine and infertility in swine. The data on the residue of the administered T‐2 toxin in domestic animals suggests that trichothecenes can be transmitted into humans.
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