| Title: | Altering the Sex Pheromone Cyclo(l-Pro-l-Pro) of the Diatom Seminavis robusta towards a Chemical Probe |
| Author(s): | Bonneure E; De Baets A; De Decker S; Van den Berge K; Clement L; Vyverman W; Mangelinckx S; |
| Address: | "Department of Green Chemistry and Technology-SynBioC, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent, Belgium. Department of Biology-Protistology and Aquatic Ecology, Faculty of Sciences, Ghent University, Krijgslaan 281/S8, 9000 Ghent, Belgium. Department of Applied Mathematics, Computer Science and Statistics, Faculty of Sciences, Ghent University, Krijgslaan 281/S9, 9000 Ghent, Belgium" |
| ISSN/ISBN: | 1422-0067 (Electronic) 1422-0067 (Linking) |
| Abstract: | "As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(l-Pro-l-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(l-Pro-l-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide- and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine- and/or azide-containing analogs to study the pheromone-detection system of S. robusta" |
| Keywords: | Biosynthetic Pathways Diatoms/*metabolism Molecular Structure Pheromones/chemistry/*metabolism Reproduction Sex Attractants/chemistry/*metabolism chemical probe diatom diazirine diketopiperazine pheromone; |
| Notes: | "MedlineBonneure, Eli De Baets, Amber De Decker, Sam Van den Berge, Koen Clement, Lieven Vyverman, Wim Mangelinckx, Sven eng BOF-GOA 01G01715/Universiteit Gent/ GOH3817N/Fonds Wetenschappelijk Onderzoek/ Switzerland 2021/01/27 Int J Mol Sci. 2021 Jan 21; 22(3):1037. doi: 10.3390/ijms22031037" |
