| Title: | Attraction Pheromone of The Benthic Diatom Seminavis robusta: Studies on Structure-Activity Relationships |
| Author(s): | Lembke C; Stettin D; Speck F; Ueberschaar N; De Decker S; Vyverman W; Pohnert G; |
| Address: | "Institute for Inorganic and Analytical Chemistry, Bioorganic Analytics, Friedrich-Schiller-Universitat Jena, Lessingstrasse 8, D-07743, Jena, Germany. Laboratory of Protistology and Aquatic Ecology, Department of Biology, University Gent, Krijgslaan 281 S8, 9000, Gent, Belgium. Institute for Inorganic and Analytical Chemistry, Bioorganic Analytics, Friedrich-Schiller-Universitat Jena, Lessingstrasse 8, D-07743, Jena, Germany. Georg.Pohnert@uni-jena.de. Max Planck Institute for Chemical Ecology, Hans-Knoll-Str. 8, D-07745, Jena, Germany. Georg.Pohnert@uni-jena.de" |
| DOI: | 10.1007/s10886-018-0944-2 |
| ISSN/ISBN: | 1573-1561 (Electronic) 0098-0331 (Linking) |
| Abstract: | "Recently the first pheromone of a marine diatom was identified to be the diketopiperazine (S,S)-diproline. This compound facilitates attraction between mating partners in the benthic diatom Seminavis robusta. Interestingly, sexualized S. robusta cells are attracted to both the natural pheromone (S,S)-diproline as well as to its enantiomer (R,R)-diproline. Usually stereospecificity is a prerequisite for successful substrate-receptor interactions, and especially pheromone perception is often highly enantioselective. Here we introduce a structure-activity relationship study, to learn more about the principles of pheromone reception in diatoms. We analyzed the activity of nine different diketopiperazines in attraction and interference assays. The pheromone diproline itself, as well as a pipecolic acid derived diketopiperazine with two expanded aliphatic ring systems, showed the highest attractivity. Hydroxylatoin of the aliphatic rings abolished any bioactivity. Diketopiperazines derived from acyclic amino acids were not attrative as well. All stereoisomers of both the diproline and the pipecolic acid derived diketopiperazine were purified by enantioselective high-performance liquid chromatography, and application in bioactivity tests confirmed that attraction pheromone perception in this diatom is indeed not stereospecific. However, the lack of activity of diketopiperazines derived from acyclic amino acids suggests a specificity that prevents misguidance to sources of other naturally occurring diketopiperazines" |
| Keywords: | "Chromatography, High Pressure Liquid Diatoms/*chemistry/metabolism Diketopiperazines/chemistry Dimerization Mass Spectrometry Pheromones/*chemistry Proline/chemistry Stereoisomerism Structure-Activity Relationship Diatoms Diketopiperazine Enantiomers Pher;" |
| Notes: | "MedlineLembke, Christine Stettin, Daniel Speck, Franziska Ueberschaar, Nico De Decker, Sam Vyverman, Wim Pohnert, Georg eng CRC 1127/SFB ChemBiosys/ TG 0374.11/Vlaamse Instelling voor Technologisch Onderzoek/ 2018/03/15 J Chem Ecol. 2018 Apr; 44(4):354-363. doi: 10.1007/s10886-018-0944-2. Epub 2018 Mar 14" |
