Structural Identification, Synthesis and Biological Activity of Two Volatile Cyclic Dipeptides in a Terrestrial Vertebrate.

Scientific Reports
Cristina Romero-DiazEmília P Martins

Abstract

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 genus Sceloporus), 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 structu...Continue Reading

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Citations

Aug 9, 2020·Behavioral Ecology : Official Journal of the International Society for Behavioral Ecology·Stephanie M CamposEmília P Martins
Jan 27, 2021·International Journal of Molecular Sciences·Eli BonneureSven Mangelinckx
Apr 1, 2021·Proceedings. Biological Sciences·Cristina Romero-DiazEmília P Martins
May 4, 2021·Integrative and Comparative Biology·Stephanie M Campos, Selma S Belkasim

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