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.
Int J Mol Sci. 2021 Jan 21;22(3):1037. doi: 10.3390/ijms22031037.
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 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 .
作为藻类的一个主要群体，硅藻在地球上的初级生产力中起着重要作用。羽纹硅藻主要是底栖生物，是物种最丰富的硅藻群体，其中 raphe 类群的成员具有运动性，通常具有异型性有性生殖。最近的研究表明，模式生物 在交配过程中使用多种性线索，包括环(l-Pro-l-Pro)作为吸引信息素。信息素检测系统的详细研究是阐明羽纹硅藻生命周期调控的一个关键方面，这可能为硅藻的物种形成提供新的基本见解。本研究报告了七种新型信息素类似物的合成和生物评价，这些类似物对环(l-Pro-l-Pro)信息素有小的结构改变。毒性、吸引力和干扰测定被应用于评估它们作为信息素的潜在活性。我们的大多数类似物表现出中等至良好的生物活性和低至无植物毒性。含叠氮化物和重氮化合物的类似物的信息素活性不受影响，并诱导出与天然信息素相似的交配行为。这些结果表明，引入受限的结构修饰可以用于开发基于重氮化合物和/或叠氮化物类似物的化学探针，以研究 的信息素检测系统。
