TY - JOUR
T1 - Structural Identification, Synthesis and Biological Activity of Two Volatile Cyclic Dipeptides in a Terrestrial Vertebrate
AU - Romero-Diaz, Cristina
AU - Campos, Stephanie M.
AU - Herrmann, Morgan A.
AU - Lewis, Kristen N.
AU - Williams, David R.
AU - Soini, Helena A.
AU - Novotny, Milos V.
AU - Hews, Diana K.
AU - Martins, Emília P.
N1 - Funding Information:
We thank Piyumika Suriyampola, Julio Rivera, Tamal Roy, Jennifer Flores and Melissa López for helpful comments on the manuscript. We are grateful to the staff at the Southwestern Research Station (of the American Museum of Natural History) for logistical support in the field. We appreciate permission from the Arizona Game and Fish Department (LIC #SP621793), US Forest Service, and Arizona State University Animal Care and Use Committee (protocol 17‐1597R to E.P.M.) to conduct this work. This material is based upon work supported by the National Science Foundation [grant numbers IOS-1050274 to E.P.M., IOS-1052247 to D.K.H. and CHE-1665356 to D.R.W.].
Publisher Copyright:
© 2020, The Author(s).
PY - 2020/12/1
Y1 - 2020/12/1
N2 - 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 structural design are crucial for biological activity, and highlight the need for more studies to determine the complete functional landscape of biologically relevant compounds.
AB - 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 structural design are crucial for biological activity, and highlight the need for more studies to determine the complete functional landscape of biologically relevant compounds.
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U2 - 10.1038/s41598-020-61312-8
DO - 10.1038/s41598-020-61312-8
M3 - Article
C2 - 32152427
AN - SCOPUS:85081635558
SN - 2045-2322
VL - 10
JO - Scientific reports
JF - Scientific reports
IS - 1
M1 - 4303
ER -