In 1974, (E)-1-nitropentadec-1-ene, a strong lipophilic contact poison of soldiers of the termite genus Prorhinotermes, was the first-described insect-produced nitro compound.1 However, its biosynthesis remained unknown. In the present study, we tested the hypothesis that (E)-1-nitropentadec-1-ene biosynthesis originates with condensation of amino acids with tetradecanoic acid. By using in vivo experiments with radiolabeled and deuterium-labeled putative precursors, we show that (E)-1-nitropentadec-1-ene is synthesized by the soldiers from glycine or l-serine and tetradecanoic acid. We propose and discuss three possible biosynthetic pathways.

Sphinganine-like biogenesis of <i>(E)</i>-1-nitropentadec-1-ene in termite soldiers of the genus <i>Prorhinotermes</i>

248th National Meeting (2014)

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Sphinganine-like biogenesis of (E)-1-nitropentadec-1-ene in termite soldiers of the genus Prorhinotermes