2-Amino-14,16-dimethyloctadecan-3-ol, a new sphingosine analogue toxin in the fungal genus Fusarium.
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.
Uhlig
Silvio
S
Department of Chemistry, National Veterinary Institute, Ullevaalsveien 68, P.O. Box 8156 Dep., 0033 Oslo, Norway.
Petersen
Dirk
D
Flåøyen
Arne
A
Wilkins
Alistair
A
D000818:Animals; D002460:Cell Line; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D005670:Fusarium / Q000737:chemistry* / Q000254:growth & development; D008401:Gas Chromatography-Mass Spectrometry; D008114:Liver Neoplasms, Experimental / Q000188:drug therapy; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009183:Mycotoxins / Q000737:chemistry / Q000633:toxicity*; D012275:Oryza / Q000382:microbiology; D051381:Rats; D021241:Spectrometry, Mass, Electrospray Ionization; D013107:Sphingolipids / Q000737:chemistry / Q000633:toxicity*; D013552:Swine; D014908:Triticum / Q000382:microbiology
D009183:Mycotoxins; D013107:Sphingolipids; C507616:2-amino-14,16-dimethyloctadecan-3-ol