New branching inhibitors and their potential as strigolactone mimics in rice
New branching inhibitors and their potential as strigolactone mimics in rice
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DOI：
10.1016/j.bmcl.2011.06.019
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发表时间：
2011-08-15
影响因子：
2.7
通讯作者：
Asami, Tadao
中科院分区：
文献类型：
--
作者：
Fukui, Kosuke;Ito, Shinsaku;Asami, Tadao
独脚金内酯是根际通讯化学物质。最近对高度分枝突变体的研究表明，SL或其代谢产物作为一种植物激素抑制枝条分枝。当SL被外源施加到水稻d10-1突变体，其具有由SL生物合成基因（CCD 8）缺陷引起的高度分枝表型时，它们抑制突变体的分蘖芽生长（水稻中的分枝）。我们将注意力集中在SL作为植物激素的功能上，并试图通过筛选抑制水稻d10-1突变体分枝的化学物质来寻找模拟SL激素作用的新化学物质。幸运的是，我们发现了5-（4-氯苯氧基）-3-甲基呋喃-2（5 H）-酮（3a）作为一种新的化学物质，对水稻d10-1突变体具有SL样活性。然后，我们制备了几种3a的衍生物（3b-3 k），以检测它们抑制水稻d10-1芽分枝的能力。这些衍生物通过酚类与卤代丁烯酮的一锅法偶联反应合成得到5-苯氧基-3-甲基呋喃-2（5 H）-酮（3）衍生物，它们具有与SL相同的结构。在水稻试验中，一些衍生物显示出比GR 24（一种典型的SL衍生物）更有效的SL样活性。由于SL还通过诱导根寄生植物的种子萌发显示活性，因此还评价了这些衍生物的诱导活性。在这里，我们报告这些化合物的构效关系。(C)2011爱思唯尔有限公司保留所有权利。
Strigolactones (SLs) are rhizosphere communication chemicals. Recent studies of highly branched mutants revealed that SL or its metabolites work as a phytohormone to inhibit shoot branching. When SLs are exogenously applied to the rice d10-1 mutant that has a highly branched phenotype caused by a defect in the SL biosynthesis gene (CCD8), they inhibit tiller bud outgrowth (branching in rice) of the mutant. We focused our attention on the SL function as a phytohormone and tried to find new chemicals mimicking the hormonal action of SL by screening chemicals that inhibit branching of rice d10-1 mutant. Fortunately, we found 5-(4-chlorophenoxy)-3-methylfuran-2(5H)-one (3a) as a new chemical possessing SL-like activity against the rice d10-1 mutant. Then, we prepared several derivatives of 3a (3b-3k) to examine their ability to inhibit shoot branching of rice d10-1. These derivatives were synthesized by a one-pot coupling reaction between phenols and halo butenolide to give 5-phenoxy 3-methylfuran-2(5H)-one (3) derivatives, which possess a common substructure with SLs. Some of the derivatives showed SL-like activity more potently than GR24, a typical SL derivative, in a rice assay. As SLs also show activity by inducing seed germination of root parasitic plants, the induction activity of these derivatives was also evaluated. Here we report the structure-activity relationships of these compounds. (C) 2011 Elsevier Ltd. All rights reserved.