title: Intrageneric differences in the four stereoisomers of stenusine in the rove beetle genus, Stenus (Coleoptera, Staphylinidae).
abstract: Most species of the rove beetle genus Stenus employ the spreading alkaloid stenusine as an escape mechanism on water surfaces. In the case of danger, they emit stenusine from their pygidial glands, and it propels them over the water very quickly. Stenusine is a chiral molecule with four stereoisomers: (2'R,3R)-, (2'S,3R)-, (2'S,3S)-, and (2'R,3S)-stenusine. The percentile ratio of these four isomers is only known for the most common species of the genus: Stenus comma. With the intention of determining the stereoisomer ratios of five additional species from the two subgenera, Stenus and Hypostenus, we used GC/mass spectrometry measurements with a chiral phase. The results showed that the ratio differs among the genus. These findings can be a basis for chemotaxonomy. It is also possible that the biological function of stenusine, e.g., as antibiotic or fungicide, varies with changing stereoisomer composition.
authors.affiliation: Department of Animal Ecology II, University of Bayreuth, 95440, Bayreuth, Germany. Inka.Lusebrink@uni-bayreuth.de
authors.forename: Inka
authors.initials: I
authors.lastname: Lusebrink
authors.forename: Dirk
authors.initials: D
authors.lastname: Burkhardt
authors.forename: Thomas
authors.initials: T
authors.lastname: Gedig
authors.forename: Konrad
authors.initials: K
authors.lastname: Dettner
authors.forename: Armin
authors.initials: A
authors.lastname: Mosandl
authors.forename: Karlheinz
authors.initials: K
authors.lastname: Seifert
mesh_terms: D000470:Alkaloids / Q000737:chemistry* / Q000378:metabolism*; D000818:Animals; D001517:Coleoptera / Q000145:classification / Q000502:physiology*; D017753:Ecosystem; D010880:Piperidines / Q000737:chemistry* / Q000378:metabolism*; D013045:Species Specificity; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D010880:Piperidines; C011112:stenusin