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

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 (EC(50)) of 16 and 24 microM, 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.

• Authors: Silvio Uhlig, Dirk Petersen, Arne Flåøyen, Alistair Wilkins
• Journal: Toxicon : official journal of the International Society on Toxinology (Toxicon) Vol. 46 Issue 5 Pg. 513-22 (Oct 2005) ISSN: 0041-0101 [Print] England
• PMID: 16084551 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Mycotoxins
• Sphingolipids
• 2-amino-14,16-dimethyloctadecan-3-ol

Topics

• Animals
• Cell Line
• Cell Line, Tumor
• Cell Survival (drug effects)
• Fusarium (chemistry, growth & development)
• Gas Chromatography-Mass Spectrometry
• Liver Neoplasms, Experimental (drug therapy)
• Magnetic Resonance Spectroscopy
• Mass Spectrometry
• Mycotoxins (chemistry, toxicity)
• Oryza (microbiology)
• Rats
• Spectrometry, Mass, Electrospray Ionization
• Sphingolipids (chemistry, toxicity)
• Swine
• Triticum (microbiology)