Intrageneric differences in the four stereoisomers of stenusine in the rove beetle genus, Stenus (Coleoptera, Staphylinidae)
Intrageneric differences in the four stereoisomers of stenusine in the rove beetle genus, Stenus (Coleoptera, Staphylinidae)
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罗夫甲虫属 Stenusine（鞘翅目、葡萄科）中 stenusine 的四种立体异构体的属内差异
DOI：
10.1007/s00114-006-0172-4
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发表时间：
2007
影响因子：
--
通讯作者：
K. Seifert
中科院分区：
文献类型：
--
作者：
I. Lusebrink;Dirk Burkhardt;Thomas Gedig;K. Dettner;A. Mosandl;K. Seifert
大多数种类的罗夫甲虫属Stenus雇用蔓延生物碱stenusine作为一种逃避机制在水面上。在危险的情况下，它们会从臀腺中释放出stenusine，这会推动它们很快地越过水面。Stenusine是一种手性分子，具有4种立体异构体：（2′R，3R）-、（2 ′S，3R）-、（2′S，3S）-和（2′R，3S）-Stenusine。这四种异构体的百分位数比率仅在该属最常见的物种中已知：Stenus comma。为了确定来自两个亚属，Stenus和Hypostenus的另外五个物种的立体异构体比率，我们使用了手性相的GC/质谱测量。结果表明，不同属间的比例不同。这些发现可以作为化学分类学的基础。也有可能stenusine的生物学功能，例如，作为抗生素或杀真菌剂，随着立体异构体组成的变化而变化。
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.