|
|||||
|
|
2-Amino-14,16-dimethyloctadecan-3-ol, a new sphingosine analogue toxin in the fungal genus Fusarium |
|
| Authors: | Silvio Uhlig Dirk Petersen Alistair Wilkins |
| Institution: | a Department of Chemistry, National Veterinary Institute, Ullevaalsveien 68, P.O. Box 8156 Dep., 0033 Oslo, Norway b Department of Chemistry, University of Oslo, P.O. Box 1033, Blindern 0315, Oslo, Norway c Chemistry Department, The University of Waikato, Private Bag 3105, Hamilton, New Zealand |
| Abstract: | 2-Amino-14,16-dimethyloctadecan-3-ol (2-AOD-3-ol) was isolated from the cytotoxic rice culture extract of a strain of Fusarium avenaceum, which had previously been isolated from Norwegian grain. The structural information was obtained from LC-MS/MS, GC-MS, NMR spectroscopy and high-resolution MS data. The metabolite has a striking similarity to sphinganine, an intermediate in the biosynthesis of the sphingolipids. This similarity is a major feature of the so-called sphingosine analogue toxins; the most studied being the AAL toxins and the fumonisins. 2-AOD-3-ol was found to be cytotoxic to the rat hepatoma cell line H4IIE-W and to the porcine epithelial kidney cell line PK(15) at concentrations (EC50) of 16 and 24 μM, respectively. The metabolite has been found in F. avenaceum inoculated wheat that was treated to support ideal conditions for Fusarium growth, demonstrating that the fungus has the potential to produce the metabolite under field conditions, which may occur in Northern Europe. |
| Keywords: | Alamar Blue assay ceramide synthase Fusarium fumonisins LC-MS mycotoxin NMR |
| 本文献已被 ScienceDirect 等数据库收录！ | |