Institute for Molecules and Materials, Cluster of Organic Chemistry, Radboud University, Nijmegen, the Netherlands.
Faculty of Science, Centre of the Region Haná for Biotechnological and Agricultural Research, Department of Chemical Biology and Genetics, Palacký University, Olomouc, Czech Republic.
Pest Manag Sci. 2019 Nov;75(11):3113-3121. doi: 10.1002/ps.5553. Epub 2019 Aug 23.
Strigolactones (SLs) have a vast number of ecological implications because of the broad spectrum of their biological activities. Unfortunately, the limited availability of SLs restricts their applicability for the benefit of humanity and renders synthesis the only option for their production. However, the structural complexity of SLs impedes their economical synthesis, which is unfeasible on a large scale. Synthesis of SL analogues and mimics with a simpler structure, but with retention of bioactivity, is the solution to this problem.
Here, we present eight new hybrid-type SL analogues derived from auxin, synthesized via coupling of auxin ester [ethyl 2-(1H-indol-3-yl)acetate] and of ethyl 2-phenylacetate with four D-rings (mono-, two di- and trimethylated). The new hybrid-type SL analogues were bioassayed to assess the germination activity of seeds of the parasitic weeds Striga hermonthica, Orobanche minor and Phelipanche ramosa using the classical method of counting germinated seeds and a colorimetric method. The bioassays revealed that analogues with a natural monomethylated D-ring had appreciable to good activity towards the three species and were the most active derivatives. By contrast, derivatives with the trimethylated D-ring showed no activity. The dimethylated derivatives (2,4-dimethyl and 3,4-dimethyl) were slightly active, especially towards P. ramosa.
New hybrid-type analogues derived from auxins have been prepared. These analogues may be attractive as potential suicidal germination agents for parasitic weed control because of their ease of preparation and relevant bioactivity. © 2019 The Authors. Pest Management Science published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.
由于其广泛的生物活性，独脚金内酯（Strigolactones，SLs）具有广泛的生态意义。不幸的是，SLs 的供应有限限制了它们对人类的应用，使其合成成为其生产的唯一选择。然而，SLs 的结构复杂性阻碍了它们的经济合成，这在大规模上是不可行的。合成具有更简单结构但保留生物活性的 SL 类似物和模拟物是解决此问题的方法。
在这里，我们提出了八种新的混合型 SL 类似物，这些类似物源自生长素，通过将生长素酯[乙基 2-（1H-吲哚-3-基）乙酸酯]和乙基 2-苯乙酸酯与四个 D-环（单，二和三甲基化）偶联合成。通过经典的计数发芽种子法和比色法，对新的混合型 SL 类似物进行了生物测定，以评估寄生杂草独脚金、列当和Phelipanche ramosa 的种子的发芽活性。生物测定表明，具有天然单甲基化 D-环的类似物对三种植物具有明显至良好的活性，是最具活性的衍生物。相比之下，具有三甲基化 D-环的衍生物没有活性。二甲基化衍生物（2,4-二甲基和 3,4-二甲基）具有轻微的活性，特别是对 P. ramosa。
已经制备了源自生长素的新型混合型类似物。由于它们易于制备和相关的生物活性，这些类似物可能作为潜在的自杀性发芽剂，用于寄生杂草的控制，具有吸引力。©2019 作者。Pest Management Science 由 John Wiley & Sons Ltd 代表化学工业协会出版。
