合成 Strigolactones 的类似物及其在溶液中稳定性的评估。

Synthesis of Analogs of Strigolactones and Evaluation of Their Stability in Solution.

机构信息

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

出版信息

Methods Mol Biol. 2021;2309:37-55. doi: 10.1007/978-1-0716-1429-7_5.

DOI:10.1007/978-1-0716-1429-7_5

PMID:34028678

Abstract

Strigolactones (SLs) are new plant hormones that play an important role in the control development of plants. They are germination stimulants for seed of parasitic weeds, are the branching factor of arbuscular mycorrhizal fungi and inhibitors for bud outgrowth and shoot branching. Natural SLs contain an annulated system of three rings (ABC scaffold) connected to a furanone (the D-ring) by an enol ether unit. The natural distribution of strigolactones is low, and their synthesis is long and difficult. Therefore, SL analogs are designed to have the same bioactiphore as natural SLs and an appreciable bioactivity. For the design a model is used based on the natural bioactiphore. Typical SL analogs are GR24, Nijmegen-1, and EM1 (derived from ethyl 2-phenylacetate). The synthesis of these SL analogs is reported together with their stability in aqueous solution.

摘要

独脚金内酯（SLs）是一类新的植物激素，在植物的生长发育调控中发挥重要作用。它们是寄生杂草种子的萌发刺激物，是丛枝菌根真菌的分枝因子，也是芽生长和侧枝分枝的抑制剂。天然 SLs 含有一个由三个环（ABC 支架）组成的稠合系统，通过烯醇醚单元与呋喃酮（D 环）相连。独脚金内酯的天然分布较低，其合成过程冗长且困难。因此，独脚金内酯类似物的设计旨在具有与天然 SLs 相同的生物活性位点和相当的生物活性。为此，设计中使用了基于天然生物活性位点的模型。典型的 SL 类似物有 GR24、Nijmegen-1 和 EM1（衍生自 2-苯基乙酸乙酯）。本文报道了这些 SL 类似物的合成方法及其在水溶液中的稳定性。