title: Detection of a new piperideine alkaloid in the pygidial glands of some Stenus beetles.
abstract: Rove beetles of the genus Stenus produce and store bioactive alkaloids like stenusine (3), 3-(2-methylbut-1-enyl)pyridine (4), and cicindeloine (5) in their pygidial glands to protect themselves from predation and microorganismic infestation. The biosynthesis of stenusine (3), 3-(2-methylbut-1-enyl)pyridine (4), and cicindeloine (5) was previously investigated in Stenus bimaculatus, Stenus similis, and Stenus solutus, respectively. The piperideine alkaloid cicindeloine (5) occurs also as a major compound in the pygidial gland secretion of Stenus cicindeloides. The three metabolites follow the same biosynthetic pathway, where the N-heterocyclic ring is derived from L-lysine and the side chain from L-isoleucine. The different alkaloids are finally obtained by few modifications of shared precursor molecules, such as 2,3,4,5-tetrahydro-5-(2-methylbutylidene)pyridine (1). This piperideine alkaloid was synthesized and detected by GC/MS and GC at a chiral phase in the pygidial glands of Stenus similis, Stenus tarsalis, and Stenus cicindeloides.
authors.affiliation: Lehrstuhl für Organische Chemie, NW II, Universität Bayreuth, DE-95440 Bayreuth, (phone: +49-921-553098; fax: +49-921-555358).
authors.forename: Isabel
authors.initials: I
authors.lastname: Wittmann
authors.affiliation: Lehrstuhl für Tierökologie II, Universität Bayreuth, DE-95440 Bayreuth.
authors.forename: Andreas
authors.initials: A
authors.lastname: Schierling
authors.affiliation: Lehrstuhl für Tierökologie II, Universität Bayreuth, DE-95440 Bayreuth.
authors.forename: Konrad
authors.initials: K
authors.lastname: Dettner
authors.affiliation: Lehrstuhl für Organische Chemie, NW II, Universität Bayreuth, DE-95440 Bayreuth, (phone: +49-921-553098; fax: +49-921-555358).
authors.forename: Matthias
authors.initials: M
authors.lastname: Göhl
authors.affiliation: Leibniz Institut für Pflanzenbiochemie, Weinberg 3, DE-06120 Halle/Saale.
authors.forename: Jürgen
authors.initials: J
authors.lastname: Schmidt
authors.affiliation: Lehrstuhl für Organische Chemie, NW II, Universität Bayreuth, DE-95440 Bayreuth, (phone: +49-921-553098; fax: +49-921-555358). karlheinz.seifert@uni-bayreuth.de.
authors.forename: Karlheinz
authors.initials: K
authors.lastname: Seifert
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D000818:Animals; D001517:Coleoptera / Q000737:chemistry*; D008401:Gas Chromatography-Mass Spectrometry; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification
chemical_list: D000470:Alkaloids; D010880:Piperidines; C576030:cicindeloine; C011112:stenusin
keywords: Biosynthesis; Piperidine alkaloids; Stenus beetles