Scenting Ketones in the Defense Glands of Two Julids From the Caucasus (Arthropoda, Myriapoda, Diplopoda, Julida).

IF 2.2 3区环境科学与生态学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Chemical Ecology Pub Date : 2025-04-29 DOI:10.1007/s10886-025-01603-4

Slobodan E Makarov, Ljubodrag Vujisić, Günther Raspotnig, Dragan Antić, Felix Anderl, Gordana Krstić, Zvezdana Jovanović, Aleksander Evsyukov, Hans S Reip, Jelena Milovanović, Bojan Ilić, Vladimir Tomić, Michaela Bodner

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引用次数: 0

Abstract

Millipedes have developed specialized chemical defenses against predators and parasites. Here we investigated the strong repellent odour emitted by two julids from the Caucasus, Syrioiulus continentalis (Attems, 1903) and Pachyiulus krivolutskyi Golovatch, 1977. By NMR and GC-MS, as well as compound synthesis, we identified the major compound in the secretions of both species as 4-ethylhex-1-en-3-one. A second compound was tentatively identified as the dimer of the main compound as 2-ethyl-1-(6-(pentan-3-yl)-3,4-dihydro-2H-pyran-2-yl)butan-1-one. Both compounds amounting for more than 95% of the whole secretion. 4-Ethylhex-1-en-3-one was found for the first time as a naturally occurring compound, and due to its identification in millipedes of the order Julida we propose here the trivial name "julidone". Considering current knowledge, the replacement of the juliform quinones by novel components such as ketones appears to be highly derived conditions in the chemistry of Julida, possibly triggered by different environmental challenges arising from the epigeic life-style of the two species.

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高加索两种菊科动物（节肢动物、多足动物、双足动物、菊科动物）防御腺中的气味酮。

千足虫已经发展出专门的化学防御系统来抵御捕食者和寄生虫。本文研究了来自高加索地区的两种鱼，Syrioiulus continentalis （atats, 1903）和Pachyiulus krivolutskyi Golovatch， 1977。通过核磁共振、气相色谱-质谱以及化合物合成，我们鉴定出两种物种分泌物中的主要化合物为4-乙基己烯-1-烯-3- 1。第二种化合物被初步鉴定为主化合物的二聚体，即2-乙基-1-（6-（戊烷-3-基）-3,4-二氢- 2h -吡喃-2-基）丁烷-1- 1。这两种化合物占全部分泌物的95%以上。4-乙基己-1-烯-3- 1是首次作为天然存在的化合物被发现，由于它在朱利达目千足虫中被发现，我们在这里提出了一个平凡的名字“朱利达”。考虑到目前的知识，朱莉叶醌被新的成分如酮取代似乎是朱莉叶化学中高度衍生的条件，可能是由两个物种的后生生活方式引起的不同环境挑战引发的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Journal of Chemical Ecology 环境科学-生化与分子生物学

CiteScore

5.10

自引率

4.30%

发文量

审稿时长

4 months

期刊介绍： Journal of Chemical Ecology is devoted to promoting an ecological understanding of the origin, function, and significance of natural chemicals that mediate interactions within and between organisms. Such relationships, often adaptively important, comprise the oldest of communication systems in terrestrial and aquatic environments. With recent advances in methodology for elucidating structures of the chemical compounds involved, a strong interdisciplinary association has developed between chemists and biologists which should accelerate understanding of these interactions in nature. Scientific contributions, including review articles, are welcome from either members or nonmembers of the International Society of Chemical Ecology. Manuscripts must be in English and may include original research in biological and/or chemical aspects of chemical ecology. They may include substantive observations of interactions in nature, the elucidation of the chemical compounds involved, the mechanisms of their production and reception, and the translation of such basic information into survey and control protocols. Sufficient biological and chemical detail should be given to substantiate conclusions and to permit results to be evaluated and reproduced.