Abstract
To protect themselves from predation and microorganismic infestation, rove beetles of the genus Stenus produce and store bioactive alkaloids like stenusine, 3-(2-methyl-1-butenyl)pyridine, and cicindeloine in their pygidial glands. The biosynthesis of stenusine and 3-(2-methyl-1-butenyl)pyridine was previously investigated in Stenus bimaculatus and Stenus similis, respectively. Both molecules 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 slight modifications of shared precursor molecules. The piperideine alkaloid cicindeloine occurs as a main compound additionally to (E)-3-(2-methyl-1-butenyl)pyridine and traces of stenusine in the pygidial gland secretion of Stenus cicindeloides and Stenus solutus. Feeding of S. solutus beetles with [D,15N]-labeled amino acids followed by GC/MS analysis techniques showed that cicindeloine is synthesized via the identical pathway and precursor molecules as the other two defensive alkaloids.
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Acknowledgments
Support of this research by a grant of the German Research Foundation (SE 595/14-1, DE 258/12-1) is gratefully acknowledged. The authors wish to thank Dr. Christoph Böttcher (Leibniz Institute of Plant Biochemistry Halle, Germany) for the ESI-QTOF-MS/MS measurements and Dr. V. Puthz (Castle Museum Schlitz, Germany) for numerous helpful hints concerning the Stenus phylogeny.
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The authors declare that the experiments performed for this article comply with the current laws of Germany.
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The authors declare that they have no conflict of interest.
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Communicated by: Sven Thatje
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Schierling, A., Dettner, K., Schmidt, J. et al. Biosynthesis of the defensive alkaloid cicindeloine in Stenus solutus beetles. Naturwissenschaften 99, 665–669 (2012). https://doi.org/10.1007/s00114-012-0945-x
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DOI: https://doi.org/10.1007/s00114-012-0945-x