Schierling Andreas, Dettner Konrad, Schmidt Jürgen, Seifert Karlheinz
Department of Animal Ecology II, University of Bayreuth, 95440, Bayreuth, Germany.
Naturwissenschaften. 2012 Aug;99(8):665-9. doi: 10.1007/s00114-012-0945-x. Epub 2012 Jul 14.
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,(15)N]-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.
为了保护自己免受捕食和微生物侵扰，Stenus属的隐翅虫会在其臀腺中产生并储存生物活性生物碱，如stenusine、3-(2-甲基-1-丁烯基)吡啶和cicindeloine。此前分别在双斑 Stenus bimaculatus和相似 Stenus similis中研究了stenusine和3-(2-甲基-1-丁烯基)吡啶的生物合成。这两种分子遵循相同的生物合成途径，其中N-杂环源自L-赖氨酸，侧链源自L-异亮氨酸。最终通过对共享前体分子的轻微修饰获得不同的生物碱。在 Cicindeloides Stenus和 Solutus Stenus的臀腺分泌物中，哌啶生物碱cicindeloine作为主要化合物，此外还有 (E)-3-(2-甲基-1-丁烯基)吡啶和痕量的stenusine。用 [D,(15)N] 标记的氨基酸喂养 Solutus Stenus甲虫，随后采用气相色谱/质谱分析技术表明，cicindeloine与其他两种防御性生物碱通过相同的途径和前体分子合成。
