Biosynthesis of Stenusine

The rove beetles of the genus Stenus Latreille synthesize the alkaloid stenusine in their pygidial glands, which are located in the last three segments of their abdomen. It is proposed that stenusine is derived from the two amino acids, l -lysine and l-isoleucine. Feeding S. bimaculatus beetles with...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 2008-05, Vol.71 (5), p.743-745
Hauptverfasser:	Lusebrink, Inka, Dettner, Konrad, Seifert, Karlheinz
Format:	Artikel
Sprache:	eng
Schlagworte:	alkaloids Alkaloids - biosynthesis Alkaloids - chemistry Animals Biochemistry. Physiology. Immunology Biological and medical sciences Coleoptera - chemistry Drosophila melanogaster Fundamental and applied biological sciences. Psychology Gas Chromatography-Mass Spectrometry Insecta Invertebrates isoleucine Isoleucine - chemistry Isoleucine - metabolism lysine Lysine - chemistry Lysine - metabolism Molecular Structure Physiology. Development Piperidines - chemistry Staphylinidae Stenus Stenus bimaculatus stenusine
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Beschreibung
Zusammenfassung:	The rove beetles of the genus Stenus Latreille synthesize the alkaloid stenusine in their pygidial glands, which are located in the last three segments of their abdomen. It is proposed that stenusine is derived from the two amino acids, l -lysine and l-isoleucine. Feeding S. bimaculatus beetles with deuterium-labeled amino acids and using GC/MS analysis showed that l -lysine forms the piperidine ring of the stenusine molecule. The side chain originates from l -isoleucine and the N-ethyl group from acetate.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np070310w