| Title |
Attraction Pheromone of The Benthic Diatom Seminavis robusta: Studies on Structure-Activity Relationships
|
|---|---|
| Published in |
Journal of Chemical Ecology, March 2018
|
| DOI | 10.1007/s10886-018-0944-2 |
| Pubmed ID | |
| Authors |
Christine Lembke, Daniel Stettin, Franziska Speck, Nico Ueberschaar, Sam De Decker, Wim Vyverman, Georg Pohnert |
| 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. |
X Demographics
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Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Netherlands | 1 | 50% |
| Germany | 1 | 50% |
Demographic breakdown
| Type | Count | As % |
|---|---|---|
| Scientists | 1 | 50% |
| Members of the public | 1 | 50% |
Mendeley readers
The data shown below were compiled from readership statistics for 21 Mendeley readers of this research output. Click here to see the associated Mendeley record.
Geographical breakdown
| Country | Count | As % |
|---|---|---|
| Unknown | 21 | 100% |
Demographic breakdown
| Readers by professional status | Count | As % |
|---|---|---|
| Student > Ph. D. Student | 6 | 29% |
| Researcher | 5 | 24% |
| Student > Master | 5 | 24% |
| Student > Doctoral Student | 2 | 10% |
| Other | 1 | 5% |
| Other | 1 | 5% |
| Unknown | 1 | 5% |
| Readers by discipline | Count | As % |
|---|---|---|
| Biochemistry, Genetics and Molecular Biology | 9 | 43% |
| Agricultural and Biological Sciences | 4 | 19% |
| Chemistry | 3 | 14% |
| Pharmacology, Toxicology and Pharmaceutical Science | 1 | 5% |
| Design | 1 | 5% |
| Other | 0 | 0% |
| Unknown | 3 | 14% |
Attention Score in Context
This research output has an Altmetric Attention Score of 2. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 26 April 2021.
All research outputs
#14,378,457
of 23,026,672 outputs
Outputs from Journal of Chemical Ecology
#1,538
of 2,055 outputs
Outputs of similar age
#189,798
of 333,763 outputs
Outputs of similar age from Journal of Chemical Ecology
#13
of 29 outputs
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