莽山蝮蛇(Protobothrops mangshanensis)的香腺成分。

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC Beilstein Journal of Organic Chemistry Pub Date : 2024-10-18 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.222
Jonas Holste, Paul Weldon, Donald Boyer, Stefan Schulz
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引用次数: 0

摘要

莽山蝮蛇(Protobothrops mangshanensis)是一种原产于中国湖南省山区的珍稀濒危蛇类。蛇类腹部有气味腺,对多个物种的气味腺进行了化学研究。这些腺体可能含有各种脂质和肽,但通常也含有复杂的羧酸混合物。我们在此报告了在动物园中生活的六只圈养个体的分泌物中发现的新型甲基支链不饱和酸。通过气相色谱-质谱(GC-MS)和气相色谱-红外(GC-IR)分析以及各种微钝化反应(包括氢化和酯化反应,生成甲基和吡啶基甲基酯),对这些化合物(4.6-dimethylalk-5-enoates)的结构(从 C11-C16 的同源系列)进行了表征。此外,二甲基噁唑啉的形成有助于双键的定位。通过合成 4,6-二甲基十二-5-烯酸甲酯,可以正确地确定结构,并显示出主要天然非对映异构体双键的 (E) 构型。与主要腺体成分胆固醇、1-O-十六烷基甘油以及其他常见的长链醇和酰胺相比,这些酸的含量很少。虽然有人提出蛇腹部气味腺具有一般防御功能,但这里报告的特殊化学成分和适量酸类可能表明莽山蝮蛇具有化学信号传递功能。此外,还首次在蛇类的气味腺中发现了含脯氨酸的二酮哌嗪,尽管不能排除可能是由分泌物中的氨基酸人工形成的。
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The scent gland composition of the Mangshan pit viper, Protobothrops mangshanensis.

The Mangshan pit viper, Protobothrops mangshanensis, is a rare, highly endangered snake native to the mountainous regions of Hunan Province in China. Snakes possess abdominal scent glands, which have been chemically studied in several species. These glands can contain various lipids and peptides, but very often also complex mixtures of carboxylic acids. We report here the occurrence of novel methyl-branched unsaturated acids found in the secretions of six captive individuals living in a zoo. The structures of these compounds, 4.6-dimethylalk-5-enoates in a homologous series from C11-C16, were characterized by GC-MS and GC-IR analysis and various microderivatization reactions including hydrogenation and esterification leading to methyl and pyridylmethyl esters. In addition, dimethyloxazoline formation helped to localize the double bond. The synthesis of methyl 4,6-dimethyldodec-5-enoate allowed the correct assignment of structures and showed the (E)-configuration of the double bond for the major naturally occurring diastereomers. These acids occur in small amounts compared to the major glandular components, cholesterol, and 1-O-hexadecylglycerol, as well as other common long-chain alcohols and amides. Although a general defensive function has been proposed for snake abdominal scent glands, the specific chemistry and moderate amounts of acids reported here may suggest a function in chemical signaling for the Mangshan pit viper. In addition, proline-containing diketopiperazines were identified for the first time in snake scent glands, although an artificial formation from amino acids likely present in the secretion cannot be excluded.

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来源期刊
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
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