Structural Identification, Synthesis and Biological Activity of Two Volatile Cyclic Dipeptides in a Terrestrial Vertebrate
Structural Identification, Synthesis and Biological Activity of Two Volatile Cyclic Dipeptides in a Terrestrial Vertebrate
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DOI：
10.1038/s41598-020-61312-8
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发表时间：
2020-03
影响因子：
4.6
通讯作者：
Cristina Romero‐Diaz;Stephanie M. Campos;Morgan A. Herrmann;Kristen N. Lewis;David R. Williams;H. Soini-H.
中科院分区：
文献类型：
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作者：
Cristina Romero‐Diaz;Stephanie M. Campos;Morgan A. Herrmann;Kristen N. Lewis;David R. Williams;H. Soini-H.
复杂的脊椎动物化学信号中的单一物质可能具有生理或行为活性。然而，化学信息素的化学结构、物理性质和分子大小的巨大多样性使得识别信息素活性化合物并非易事。本文从陆生脊椎动物（蜥蜴属Sceloporus）的复杂化学信号混合物中鉴定出两种挥发性环二肽cyclo（L-Leu-L-Pro）和cyclo（L-Pro-L-Pro），合成了其中一种，并研究了它们在雄性种内通讯中的生物活性。在一系列行为试验中，与对照组、环状（L-Leu-L-Pro）共混物或具有两种环状二肽的组合共混物相比，当呈现合成的环状（L-Pro-L-Pro）化学共混物时，蜥蜴表现出更多的化学感觉行为（舌头轻弹、嘴唇拍击和基底舔）。结果表明，环（L-Pro-L-Pro）和环（L-Leu-L-Pro）的调节作用，可能取决于化学信号中的两种化合物的相对浓度的潜在的化学信息素的作用。此外，我们的研究结果强调了复杂混合物中的次要化合物如何产生有意义的行为反应，结构设计中的微小差异对生物活性至关重要，并强调需要进行更多的研究来确定生物相关化合物的完整功能景观。
Single substances within complex vertebrate chemical signals could be physiologically or behaviourally active. However, the vast diversity in chemical structure, physical properties and molecular size of semiochemicals makes identifying pheromonally active compounds no easy task. Here, we identified two volatile cyclic dipeptides, cyclo(L-Leu-L-Pro) and cyclo(L-Pro-L-Pro), from the complex mixture of a chemical signal in terrestrial vertebrates (lizard genusSceloporus), synthesised one of them and investigated their biological activity in male intra-specific communication. In a series of behavioural trials, lizards performed more chemosensory behaviour (tongue flicks, lip smacks and substrate lickings) when presented with the synthesised cyclo(L-Pro-L-Pro) chemical blend, compared to the controls, the cyclo(L-Leu-L-Pro) blend, or a combined blend with both cyclic dipeptides. The results suggest a potential semiochemical role of cyclo(L-Pro-L-Pro) and a modulating effect of cyclo(L-Leu-L-Pro) that may depend on the relative concentration of both compounds in the chemical signal. In addition, our results stress how minor compounds in complex mixtures can produce a meaningful behavioural response, how small differences in structural design are crucial for biological activity, and highlight the need for more studies to determine the complete functional landscape of biologically relevant compounds.