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Wittmann, Isabel ; Schierling, Andreas ; Dettner, Konrad ; Göhl, Matthias ; Schmidt, Jürgen ; Seifert, Karlheinz:
Detection of a New Piperideine Alkaloid in the Pygidial Glands of Some Stenus Beetles.
In: Chemistry & Biodiversity.
Bd. 12
(2015)
Heft 9
.
- S. 1422-1434.
ISSN 1612-1880
DOI: https://doi.org/10.1002/cbdv.201400391
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 frompredation and microorganismic infestation.The biosynthesis of stenusine (3), 3-(2-methylbut-1-enyl)pyridine (4), and cicindeloine (5) was previouslyinvestigated in Stenus bimaculatus, Stenus similis, and Stenus solutus, respectively. The piperideinealkaloid cicindeloine (5) occurs also as a major compound in the pygidial gland secretion of Stenuscicindeloides. The three metabolites follow the same biosynthetic pathway, where the N-heterocyclic ringis derived from l-lysine and the side chain from l-isoleucine. The different alkaloids are finally obtainedby 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 phasein the pygidial glands of Stenus similis, Stenus tarsalis, and Stenus cicindeloides.