Sphinganine-like biogenesis of (E)-1-nitropentadec-1-ene in termite soldiers of the genus Prorhinotermes.
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.
Institute of Organic Chemistry and Biochemistry, Flemingovo n. 2, 166 10 Prague (Czech Republic).
Anna
A
Jirošová
Pavel
P
Majer
Andrej
A
Jančařík
Klára
K
Dolejšová
Richard
R
Tykva
Jan
J
Sobotník
Pavel
P
Jiroš
Robert
R
Hanus
D000596:Amino Acids / Q000737:chemistry / Q000378:metabolism; D000818:Animals; D003903:Deuterium / Q000737:chemistry; D020049:Isoptera / Q000737:chemistry* / Q000378:metabolism; D007553:Isotope Labeling; D019814:Myristic Acid / Q000737:chemistry / Q000378:metabolism; D009281:Naphthalenes / Q000737:chemistry / Q000378:metabolism*; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
D000596:Amino Acids; D009281:Naphthalenes; D019814:Myristic Acid; C016614:1-nitronaphthalene; D003903:Deuterium; D013110:Sphingosine; C005682:safingol
Prorhinotermes; biosynthesis; natural products; nitro compounds; termites