title: Biosynthesis of the defensive alkaloid (Z)-3-(2-methyl-1-butenyl)pyridine in Stenus similis beetles.
abstract: Most rove beetles of the genus Stenus protect themselves against microorganisms and predators such as ants and spiders by producing the alkaloid stenusine (1) in their pygidial glands. The biosynthesis of 1 was previously investigated in S. bimaculatus, where L-lysine forms the piperidine ring, L-isoleucine the side chain, and acetate the N-ethyl group. In addition to 1, S. similis keeps the pyridine alkaloid (Z)-3-(2-methyl-1-butenyl)pyridine (2) in its pygidial glands. Feeding S. similis beetles with [D,15N]-labeled amino acids followed by GC/MS analysis showed that L-Lys yields the pyridine ring and L-Ile the 2-methyl-1-butenyl side chain. Thus the alkaloids 1 and 2 probably share two precursor molecules in their biosynthesis.
authors.affiliation: Department of Animal Ecology II, University of Bayreuth, Germany. andreas.schierling@uni-bayreuth.de
authors.forename: Andreas
authors.initials: A
authors.lastname: Schierling
authors.forename: Matthias
authors.initials: M
authors.lastname: Schott
authors.forename: Konrad
authors.initials: K
authors.lastname: Dettner
authors.forename: Karlheinz
authors.initials: K
authors.lastname: Seifert
mesh_terms: D000470:Alkaloids / Q000096:biosynthesis* / Q000737:chemistry / Q000494:pharmacology; D000818:Animals; D001517:Coleoptera / Q000378:metabolism*; D008401:Gas Chromatography-Mass Spectrometry; D005858:Germany; D007532:Isoleucine / Q000378:metabolism; D008239:Lysine / Q000378:metabolism; D015394:Molecular Structure; D010880:Piperidines / Q000737:chemistry / Q000494:pharmacology; D011725:Pyridines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: C569079:(Z)-3-(2-methyl-1-butenyl)pyridine; D000470:Alkaloids; D010880:Piperidines; D011725:Pyridines; D007532:Isoleucine; C011112:stenusin; D008239:Lysine