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Biosynthesis of the Defensive Alkaloid (Z)-3-(2-Methyl-1-butenyl)pyridine in Stenus similis Beetles

Title data

Schierling, Andreas ; Schott, Matthias ; Dettner, Konrad ; Seifert, Karlheinz:
Biosynthesis of the Defensive Alkaloid (Z)-3-(2-Methyl-1-butenyl)pyridine in Stenus similis Beetles.
In: Journal of Natural Products. Vol. 74 (2011) Issue 10 . - pp. 2231-2234.
ISSN 1520-6025
DOI: https://doi.org/10.1021/np200621d

Abstract in another language

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.

Further data

Item Type: Article in a journal
Refereed: Yes
Additional notes: BAYCEER101356
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 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
Research Institutions
Research Institutions > Research Centres
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: 29 Apr 2015 15:42
Last Modified: 15 Apr 2020 07:40
URI: https://eref.uni-bayreuth.de/id/eprint/11704