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千足虫(多足纲,倍足纲)的化学防御:布兰纽虫科的物种属于“醌类”进化枝吗?

Chemical defense in millipedes (Myriapoda, Diplopoda): do representatives of the family Blaniulidae belong to the 'quinone' clade?

作者信息

Vujisić Ljubodrag V, Antić Dragan Ž, Vučković Ivan M, Sekulić Tatjana Lj, Tomić Vladimir T, Mandić Boris M, Tešević Vele V, Ćurčić Božidar P M, Vajs Vlatka E, Makarov Slobodan E

机构信息

Faculty of Chemistry, University of Belgrade, Studentski trg 12 - 16, 11000 Belgrade, Serbia.

出版信息

Chem Biodivers. 2014 Mar;11(3):483-90. doi: 10.1002/cbdv.201300355.

DOI:10.1002/cbdv.201300355
PMID:24634077
Abstract

The defensive secretions of two blaniulid millipedes, Nopoiulus kochii and Cibiniulus phlepsii, were characterized by GC-FID and GC/MS analyses, which showed the presence of a complex mixture of benzoquinones, hydroquinones, and oleates. Altogether, 13 compounds were identified. The major compound in the secretions of both analyzed species was 2-methyl-1,4-benzoquinone (toluquinone). The second major constituent in the N. kochii secretion was 2-methyl-3,4-(methylenedioxy)phenol, while in that of C. phlepsii, it was 2-methoxy-3-methyl-1,4-benzoquinone. The defensive secretion of N. kochii also showed a high content of hydroquinones (13.5%) in comparison to that of C. phlepsii (0.8%). Hexyl oleate and octyl oleate were detected for the first time in defensive millipede fluids. The chemical composition of the defensive secretions supports the chemotaxonomic position of the family Blaniulidae in the 'quinone' millipede clade.

摘要

通过气相色谱-氢火焰离子化检测器(GC-FID)和气相色谱/质谱联用(GC/MS)分析,对两种球马陆(Nopoiulus kochii和Cibiniulus phlepsii)的防御性分泌物进行了表征,结果显示其中存在苯醌、对苯二酚和油酸酯的复杂混合物。总共鉴定出了13种化合物。两种被分析物种分泌物中的主要化合物均为2-甲基-1,4-苯醌(甲苯醌)。N. kochii分泌物中的第二主要成分是2-甲基-3,4-(亚甲二氧基)苯酚,而在C. phlepsii分泌物中则是2-甲氧基-3-甲基-1,4-苯醌。与C. phlepsii(0.8%)相比,N. kochii的防御性分泌物中对苯二酚的含量也很高(13.5%)。首次在球马陆的防御性分泌物中检测到己基油酸酯和辛基油酸酯。防御性分泌物的化学成分支持了球马陆科在“醌类”马陆进化枝中的化学分类学地位。

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