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新型独脚金内酯类似物:作为发芽刺激剂对寄生杂草的结构活性关系和作用模式。

New strigolactone mimics: structure-activity relationship and mode of action as germinating stimulants for parasitic weeds.

机构信息

Radboud University Nijmegen, Institute for Molecules and Materials, Cluster of Organic Chemistry, Nijmegen, The Netherlands.

出版信息

Bioorg Med Chem Lett. 2013 Sep 15;23(18):5182-6. doi: 10.1016/j.bmcl.2013.07.004. Epub 2013 Jul 13.

Abstract

Strigolactones (SLs) are new plant hormones with varies important bio-functions. This Letter deals with germination of seeds of parasitic weeds. Natural SLs have a too complex structure for synthesis. Therefore, there is an active search for SL analogues and mimics with a simpler structure with retention of activity. SL analogues all contain the D-ring connected with an enone moiety through an enol ether unit. A new mechanism for the hydrolysis SL analogues involving bidentate bound water and an α,β-hydrolase with a Ser-His-Asp catalytic triad has been proposed. Newly discovered SL mimics only have the D-ring with an appropriate leaving group at C-5. A mode of action for SL mimics was proposed for which now supporting evidence is provided. As predicted an extra methyl group at C-4 of the D-ring blocks the germination of seeds of parasitic weeds.

摘要

独脚金内酯是具有各种重要生物功能的新型植物激素。这封信涉及寄生杂草种子的萌发。天然独脚金内酯的结构过于复杂,无法进行合成。因此,人们积极寻找结构更简单但保留活性的独脚金内酯类似物和模拟物。独脚金内酯类似物都含有 D 环,通过烯醇醚单元与 C-2 位上的烯酮部分连接。提出了一种新的独脚金内酯类似物水解机制,涉及桥连双配位水分子和具有 Ser-His-Asp 催化三联体的α,β-水解酶。新发现的独脚金内酯模拟物仅在 D 环的 C-5 位上具有适当的离去基团。提出了独脚金内酯模拟物的作用模式,现在提供了支持该模式的证据。正如预测的那样,D 环 C-4 位上的额外甲基基团阻止了寄生杂草种子的萌发。

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