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Altering the sex pheromone cyclo(L-Pro-L-Pro) of the diatom Seminavis robusta towards a chemical probe

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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
diatom, pheromone, diketopiperazine, chemical probe, diazirine

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MLA
Bonneure, Eli, et al. “Altering the Sex Pheromone Cyclo(L-Pro-L-Pro) of the Diatom Seminavis Robusta towards a Chemical Probe.” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, vol. 22, no. 3, 2021, doi:10.3390/ijms22031037.
APA
Bonneure, E., De Baets, A., De Decker, S., Van den Berge, K., Clement, L., Vyverman, W., & Mangelinckx, S. (2021). Altering the sex pheromone cyclo(L-Pro-L-Pro) of the diatom Seminavis robusta towards a chemical probe. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 22(3). https://doi.org/10.3390/ijms22031037
Chicago author-date
Bonneure, Eli, Amber De Baets, Sam De Decker, Koen Van den Berge, Lieven Clement, Wim Vyverman, and Sven Mangelinckx. 2021. “Altering the Sex Pheromone Cyclo(L-Pro-L-Pro) of the Diatom Seminavis Robusta towards a Chemical Probe.” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES 22 (3). https://doi.org/10.3390/ijms22031037.
Chicago author-date (all authors)
Bonneure, Eli, Amber De Baets, Sam De Decker, Koen Van den Berge, Lieven Clement, Wim Vyverman, and Sven Mangelinckx. 2021. “Altering the Sex Pheromone Cyclo(L-Pro-L-Pro) of the Diatom Seminavis Robusta towards a Chemical Probe.” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES 22 (3). doi:10.3390/ijms22031037.
Vancouver
1.
Bonneure E, De Baets A, De Decker S, Van den Berge K, Clement L, Vyverman W, et al. Altering the sex pheromone cyclo(L-Pro-L-Pro) of the diatom Seminavis robusta towards a chemical probe. INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES. 2021;22(3).
IEEE
[1]
E. Bonneure et al., “Altering the sex pheromone cyclo(L-Pro-L-Pro) of the diatom Seminavis robusta towards a chemical probe,” INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, vol. 22, no. 3, 2021.
@article{8689367,
  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.}},
  articleno    = {{1037}},
  author       = {{Bonneure, Eli and De Baets, Amber and De Decker, Sam and Van den Berge, Koen and Clement, Lieven and Vyverman, Wim and Mangelinckx, Sven}},
  issn         = {{1422-0067}},
  journal      = {{INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES}},
  keywords     = {{diatom,pheromone,diketopiperazine,chemical probe,diazirine}},
  language     = {{eng}},
  number       = {{3}},
  pages        = {{14}},
  title        = {{Altering the sex pheromone cyclo(L-Pro-L-Pro) of the diatom Seminavis robusta towards a chemical probe}},
  url          = {{http://dx.doi.org/10.3390/ijms22031037}},
  volume       = {{22}},
  year         = {{2021}},
}

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