Sphinganine-like biogenesis of (E)-1-nitropentadec-1-ene in termite soldiers of the genus Prorhinotermes
Language English Country Germany Media print-electronic
Document type Journal Article, Research Support, Non-U.S. Gov't
- Keywords
- Prorhinotermes, biosynthesis, natural products, nitro compounds, termites,
- MeSH
- Amino Acids chemistry metabolism MeSH
- Deuterium chemistry MeSH
- Isoptera chemistry metabolism MeSH
- Isotope Labeling MeSH
- Myristic Acid chemistry metabolism MeSH
- Naphthalenes chemistry metabolism MeSH
- Sphingosine analogs & derivatives chemistry MeSH
- Stereoisomerism MeSH
- Animals MeSH
- Check Tag
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- 1-nitronaphthalene MeSH Browser
- Amino Acids MeSH
- Deuterium MeSH
- Myristic Acid MeSH
- Naphthalenes MeSH
- safingol MeSH Browser
- Sphingosine MeSH
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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