2-Amino-14,16-dimethyloctadecan-3-ol, a new sphingosine analogue toxin in the fungal genus Fusarium

Uhlig, Silvio; Petersen, Dirk; Flåøyen, A.; Wilkins, Alistair L.

doi:10.1016/j.toxicon.2005.06.016

Cited by 34 publications

(30 citation statements)

References 13 publications

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“…Consequently, ENN concentrations were positively correlated to other metabolites that are likely to originate from the same fungus, e.g., MON (strongest correlation in wheat) (Figure 2). Another metabolite, produced by F. avenaceum , is the sphinganine analogue 2-AOD-3-ol [24]. Occurrence data for this compound were so far practically missing.…”

Section: Resultsmentioning

confidence: 99%

Faces of a Changing Climate: Semi-Quantitative Multi-Mycotoxin Analysis of Grain Grown in Exceptional Climatic Conditions in Norway

Uhlig

Eriksen

Hofgaard³

et al. 2013

Toxins

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Recent climatological research predicts a significantly wetter climate in Southern Norway as a result of global warming. Thus, the country has already experienced unusually wet summer seasons in the last three years (2010–2012). The aim of this pilot study was to apply an existing multi-analyte LC-MS/MS method for the semi-quantitative determination of 320 fungal and bacterial metabolites in Norwegian cereal grain samples from the 2011 growing season. Such knowledge could provide important information for future survey and research programmes in Norway. The method includes all regulated and well-known mycotoxins such as aflatoxins, trichothecenes, ochratoxin A, fumonisins and zearalenone. In addition, a wide range of less studied compounds are included in the method, e.g., Alternaria toxins, ergot alkaloids and other metabolites produced by fungal species within Fusarium, Penicillium and Aspergillus. Altogether, 46 metabolites, all of fungal origin, were detected in the 76 barley, oats and wheat samples. The analyses confirmed the high prevalence and relatively high concentrations of type-A and -B trichothecenes (e.g., deoxynivalenol up to 7230 µg/kg, HT-2 toxin up to 333 µg/kg). Zearalenone was also among the major mycotoxins detected (maximum concentration 1670 µg/kg). Notably, several other Fusarium metabolites such as culmorin, 2-amino-14,16-dimethyloctadecan-3-ol and avenacein Y were co-occurring. Furthermore, the most prevalent Alternaria toxin was alternariol with a maximum concentration of 449 µg/kg. A number of Penicillium and Aspergillus metabolites were also detected in the samples, e.g., sterigmatocystin in concentrations up to 20 µg/kg.

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Section: Resultsmentioning

confidence: 99%

Faces of a Changing Climate: Semi-Quantitative Multi-Mycotoxin Analysis of Grain Grown in Exceptional Climatic Conditions in Norway

Uhlig

Eriksen

Hofgaard³

et al. 2013

Toxins

Self Cite

125

112

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“…which are known to produce mycotoxins [12,13], the non-identification of any conventional phycotoxins in contaminated samples, and the evidence from the retention time together with the mass accuracy close to 1 ppm of the toxic compound and C17-SPA shows that the compound responsible for the toxicity of mussels collected from shellfish farming areas in Bizerte Lagoon is unequivocally a mycotoxin structurally similar to C17-SPA. This toxin was thus named C17-sphinganine analog mycotoxin (C17-SAMT).…”

Section: Resultsmentioning

confidence: 99%

Toxic C17-Sphinganine Analogue Mycotoxin, Contaminating Tunisian Mussels, Causes Flaccid Paralysis in Rodents

Marrouchi

Benoit

Caër³

et al. 2013

Marine Drugs

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Severe toxicity was detected in mussels from Bizerte Lagoon (Northern Tunisia) using routine mouse bioassays for detecting diarrheic and paralytic toxins not associated to classical phytoplankton blooming. The atypical toxicity was characterized by rapid mouse death. The aim of the present work was to understand the basis of such toxicity. Bioassay-guided chromatographic separation and mass spectrometry were used to detect and characterize the fraction responsible for mussels’ toxicity. Only a C17-sphinganine analog mycotoxin (C17-SAMT), with a molecular mass of 287.289 Da, was found in contaminated shellfish. The doses of C17-SAMT that were lethal to 50% of mice were 750 and 150 μg/kg following intraperitoneal and intracerebroventricular injections, respectively, and 900 μg/kg following oral administration. The macroscopic general aspect of cultures and the morphological characteristics of the strains isolated from mussels revealed that the toxicity episodes were associated to the presence of marine microfungi (Fusarium sp., Aspergillus sp. and Trichoderma sp.) in contaminated samples. The major in vivo effect of C17-SAMT on the mouse neuromuscular system was a dose- and time-dependent decrease of compound muscle action potential amplitude and an increased excitability threshold. In vitro, C17-SAMT caused a dose- and time-dependent block of directly- and indirectly-elicited isometric contraction of isolated mouse hemidiaphragms.

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“…The procedure for the isolation of the putative fumonisin-like compounds from the f um6 mutant cultures was based on that for the isolation of 2-amino-12,16-dimethyloctadecan-3-ol from cultures of F. avenaceum. 24 The procedure proved to be effective for the metabolites produced by the f um6 mutants. However, even though the use of a silanol-shielded sorbent during final separation of fumonisin-like compounds was favorable for peak shape and resolution of individual compounds, baseline separation of the three m/z 374 compounds could not be achieved on a semipreparative scale.…”

Section: ■ Materials and Methodsmentioning

confidence: 96%

Identification of Early Fumonisin Biosynthetic Intermediates by Inactivation of the FUM6 Gene in Fusarium verticillioides

Uhlig

Busman

Shane

et al. 2012

J. Agric. Food Chem.

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Fumonisins are polyketide mycotoxins produced by the maize pathogen Fusarium verticillioides and are associated with multiple human and animal diseases. A fumonisin biosynthetic pathway has been proposed, but structures of early pathway intermediates have not been demonstrated. The F. verticillioides FUM6 gene is required for an early pathway step. Here, metabolites produced by strains of the fungus with an inactivated FUM6 gene were purified and shown by mass spectrometry and NMR spectroscopy to have fumonisin-like structures but without substitutions at C-14 and C-15. The major metabolite was 2-amino-12,16-dimethylicosane-3,10-diol. Lesser amounts of 3-keto and triol analogues of the metabolite were also identified. In precursor feeding experiments, 2-amino-12,16-dimethylicosane-3,10-diol was transformed to fumonisins by a F. verticillioides strain with an inactive fumonisin polyketide synthase gene. The results support the hypothesis that the FUM6-encoded enzyme catalyzes fumonisin C-14 and C-15 hydroxylation and provide direct spectroscopic and biochemical evidence for structures of early intermediates in fumonisin biosynthesis.

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2-Amino-14,16-dimethyloctadecan-3-ol, a new sphingosine analogue toxin in the fungal genus Fusarium

Cited by 34 publications

References 13 publications

Faces of a Changing Climate: Semi-Quantitative Multi-Mycotoxin Analysis of Grain Grown in Exceptional Climatic Conditions in Norway

Faces of a Changing Climate: Semi-Quantitative Multi-Mycotoxin Analysis of Grain Grown in Exceptional Climatic Conditions in Norway

Toxic C17-Sphinganine Analogue Mycotoxin, Contaminating Tunisian Mussels, Causes Flaccid Paralysis in Rodents

Identification of Early Fumonisin Biosynthetic Intermediates by Inactivation of the FUM6 Gene in Fusarium verticillioides

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