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Detection of a New Piperideine Alkaloid in the Pygidial Glands of Some Stenus Beetles

Title data

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. Vol. 12 (2015) Issue 9 . - pp. 1422-1434.
ISSN 1612-1880
DOI: https://doi.org/10.1002/cbdv.201400391

Abstract in another language

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.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: BAYCEER131826
Institutions of the University: Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Chair Animal Ecology II - Evolutionary Animal Ecology
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors > Chair Animal Ecology II - Univ.-Prof. Dr. Konrad Dettner
Research Institutions
Research Institutions > Research Centres
Research Institutions > Research Centres > Bayreuth Center of Ecology and Environmental Research- BayCEER
Faculties
Faculties > Faculty of Biology, Chemistry and Earth Sciences
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology
Faculties > Faculty of Biology, Chemistry and Earth Sciences > Department of Biology > Former Professors
Result of work at the UBT: Yes
DDC Subjects: 500 Science
Date Deposited: 05 Aug 2016 07:29
Last Modified: 05 Aug 2016 07:29
URI: https://eref.uni-bayreuth.de/id/eprint/33833