Sphinganine‐Like Biogenesis of (E)‐1‐Nitropentadec‐1‐ene in Termite Soldiers of the Genus Prorhinotermes |
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| Authors: | Dr Anna Jiro?ová Dr Pavel Majer Andrej Jan?a?ík Klára Dolej?ová Dr Richard Tykva Dr Jan ?obotník Dr Pavel Jiro? Dr Robert Hanus |
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| Affiliation: | 1. Institute of Organic Chemistry and Biochemistry, Flemingovo n. 2, 166 10 Prague (Czech Republic);2. Faculty of Science, Charles University in Prague, Vini?ná 7, 128 44 Prague (Czech Republic);3. Faculty of Forestry and Wood Sciences, Czech University of Life Sciences, Kamycká 1176, 165 21 Prague (Czech Republic) |
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| Abstract: | 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. 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. |
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| Keywords: | biosynthesis natural products nitro compounds Prorhinotermes termites |
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