@Article{IPB-1173,
author = {Wittmann, I. and Schierling, A. and Dettner, K. and Göhl, M. and Schmidt, J. and Seifert, K.},
title = {{Detection of a New Piperideine Alkaloid in the Pygidial Glands of Some Stenus Beetles}},
year = {2015},
pages = {1422-1434},
journal = {Chem. Biodivers.},
doi = {10.1002/cbdv.201400391},
volume = {12},
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.}    
}