Millipedes (Diplopoda) are well known for their toxic or repellent defensive secretions. Here we describe gosodesmine (1), 7-(4-methylpent-3-en-1-yl)-1,2,3,5,8,8a-hexahydroindolizine, a unique alkaloid with some terpene character found in the chemical defense secretions of the millipede Gosodesmus claremontus Chamberlin (Colobognatha, Platydesmida, Andrognathidae). The structure of 1 was suggested by its mass spectra and GC-FTIR spectra and established from its ¹H, ¹³C, and 2D NMR spectra and 1D NOE studies. The 7-substituted indolizidine carbon skeleton of 1 was confirmed by unambiguous synthesis. This is the first report of an alkaloid from a platydesmid millipede and the first report of a 7-substituted indolizidine from an arthropod.

中文翻译：

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Gosodesmine，一种来自千足虫 Gosodesmus claremontus 的 7-取代六氢茚茚。

千足虫（Diplopoda）以其有毒或具有排斥性的防御性分泌物而闻名。在这里，我们描述了 gosodesmine ( 1 ), 7-(4-methylpent-3-en-1-yl)-1,2,3,5,8,8a-hexahydroindolizine，一种在化学防御中发现的具有某些萜烯特征的独特生物碱千足虫Gosodesmus claremontus Chamberlin (Colobognatha, Platydesmida, Andrognathidae) 的分泌物。1的结构由其质谱和 GC-FTIR 光谱提出，并由其¹ H、¹³ C 和 2D NMR 光谱和 1D NOE 研究确定。的7-取代的吲嗪啶的碳骨架1经明确合成证实。这是来自鸭嘴兽千足虫的生物碱的第一份报告和来自节肢动物的 7-取代吲哚里西啶的第一份报告。