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Structure Elucidation of the First Sex-Inducing Pheromone of a Diatom |
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| Authors: | Franziska A Klapper Dr Christine Kiel Dr Peter Bellstedt Prof?Dr Wim Vyverman Prof?Dr Georg Pohnert |
| Institution: | 1. Institute for Inorganic and Analytical Chemistry, Bioorganic Analytics, Friedrich Schiller University Jena, Lessingstrasse 8, 07743 Jena, Germany;2. Institute for Inorganic and Analytical Chemistry, Bioorganic Analytics, Friedrich Schiller University Jena, Lessingstrasse 8, 07743 Jena, Germany
Department of Plankton and Microbial Ecology, Leibniz Institute of Freshwater Ecology and Inland Fisheries, Zur alten Fischerhütte 2, 16775 Stechlin, Germany;3. Institute of Organic and Macromolecular Chemistry, Friedrich Schiller University Jena, Humboldtstraße 10, 07743 Jena, Germany Institute of Clinical Chemistry, University of Zurich & University Hospital, Rämistrasse 100, 8091 Zürich, Switzerland;4. Laboratory of Protistology and Aquatic Ecology, Department of Biology, Ghent University, Krijgslaan 281 S8, 9000 Ghent, Belgium |
| Abstract: | Diatoms are abundant unicellular microalgae, responsible for ≈20 % of global photosynthetic CO2 fixation. Nevertheless, we know little about fundamental aspects of their biology, such as their sexual reproduction. Pheromone-mediated chemical communication is crucial for successful mating. An attraction pheromone was identified in the diatom Seminavis robusta, but metabolites priming cells for sex and synchronizing search and mating behavior remained elusive. These sex-inducing pheromones (SIP) induce cell cycle arrest and trigger the production of the attraction pheromone. Here we describe the challenging structure elucidation of an S. robusta SIP. Guided by metabolomics, a candidate metabolite was identified and elucidated by labeling experiments, NMR, ESI MSn analyses, and chemical transformations. The use of negative ion mode MS was essential to decipher the unprecedented hydroxyproline and β-sulfated aspartate-containing cyclic heptapeptide that acts in femtomolar concentrations. |
| Keywords: | Cell Cycle Arrest Diatoms Marine Biofilms Peptide Sex Pheromone Structure Elucidation |