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The scent gland chemistry of neogoveid cyphophthalmids (Opiliones): an unusual methyljuglone from Metasiro savannahensis.
Chemoecology ( IF 1.8 ) Pub Date : 2019-09-26 , DOI: 10.1007/s00049-019-00288-y
Günther Raspotnig 1 , Felix Anderl 1 , Ronald M Clouse 2, 3
Affiliation  

While the chemistries of scent gland secretions from a few selected species of three families of Cyphophthalmi, namely Sironidae, Pettalidae, and Stylocellidae, have already been reported and found to consist of complex blends of naphthoquinones and methyl ketones, nothing is known about the other families. We here report on the secretions of Metasiro savannahensis Clouse and Wheeler (Zootaxa 3814:177–201, 2014), a first representative of the family Neogoveidae. The secretions from males, females and one juvenile were extracted and analyzed by gas chromatography–mass spectrometry. Twenty-five compounds were identified, all of which belong to the chemical classes of naphthoquinones and methyl ketones, confirming a hypothesized chemical uniformity of cyphophthalmid exudates. One major naphthoquinone compound, however, was new for cyphophthalmids and for arthropod exocrine secretions in general: a methyljuglone isomer, 6-methyljuglone (= 6-MJ; iupac name: 5-hydroxy-6-methyl-1,4-naphthoquinone), amounted for about 20% of the secretion and was eventually identified by synthesis. Hydroxy-naphthoquinones and their derivatives are known to possess a variety of antibiotic effects, probably enhancing the antimicrobial/antifungal potential of the Metasiro-secretion. Currently, without further data on neogoveids, the compound represents a chemical autapomorphy of M. savannahensis, and—just as the strange chloro-naphthoquinones of Sironidae and Pettalidae—adds to the repertoire of unusual naphthoquinone compounds across the Cyphophthalmi.

中文翻译:

新果夫环磷酰胺(Opiliones)的气味腺化学:来自萨凡纳西(Metasiro savannahensis)的一种不寻常的甲基胡胶。

虽然已经报道了氯酞phthal三个科的几个选定物种的气味腺分泌物的化学物质,即Sironidae,Petalidae和Stylocellidae,并且它们由萘醌和甲基酮的复杂混合物组成,但其他家族一无所知。我们在这里报告大头草的分泌Clouse和Wheeler(Zootaxa 3814:177–201,2014年),新足纲科的第一个代表。提取男性,女性和一名少年的分泌物,并通过气相色谱-质谱法进行分析。鉴定出二十五种化合物,所有这些化合物均属于萘醌和甲基酮的化学类别,从而证实了环酞酰胺渗出液的假定化学均一性。但是,一种主要的萘醌化合物对于环酞和节肢动物的外分泌通常是新的:甲基juglone异构体,6-methyljuglone(= 6-MJ; iupac名称:5-hydroxy-6-methyl-1,4-naphthoquinone),约占分泌物的20%,并最终通过合成鉴定。众所周知,羟基萘醌及其衍生物具有多种抗生素作用,Metasiro分泌物。目前,在没有关于新卵泡类的进一步数据的情况下,该化合物代表了热带稀树霉菌的化学自噬型,并且就像沙丁鱼科和Pet科的奇怪的氯萘醌一样,也增加了跨酞菁的非常规萘醌类化合物的种类。
更新日期:2019-09-26
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