Graduate School of Agriculture , Ehime University , 3-5-7 Tarumi , Matsuyama , Ehime 790-8566 , Japan.
J Agric Food Chem. 2018 May 2;66(17):4551-4558. doi: 10.1021/acs.jafc.8b01948. Epub 2018 Apr 23.
The relationship between the structure of lignano-9,9'-lactone (2,3-dibenzylbutyrolactone) and its activity as a plant growth regulator has been clarified. Derivatives with higher plant growth inhibitory activity than natural dimethylmatairesinol 4 were synthesized. The 2-hydroxy-7- Z-ene derivative 42 displayed growth inhibitory activity against both the shoots (IC = 0.65 mM) and roots (IC = 0.43 mM) of lettuce seedlings. Regiospecific activity was observed. The 2,3-dihydroxy derivative 24 showed the highest growth inhibitory activity against both the shoots (IC = 0.36 mM) and roots (IC = 0.13 mM) of Italian ryegrass seedlings. A similar level of activity to 24 against just the roots of Italian ryegrass seedlings was maintained when the hydroxy group at position 3 of the 2,3-dihydroxy derivative 24 was replaced by a fluorine atom. The (2-hydroxy,4-fluoro)-derivative 33 also showed growth inhibitory activity against both the shoots (IC = 0.79 mM) and roots (IC = 0.14 mM) of Italian ryegrass seedlings. The level of activity was found to depend on the positions of the two hydroxy groups or the hydroxy group and fluorine atom on the aromatic ring. The importance of the lignano-9,9'-lactone structure was also shown.
已阐明木脂素-9,9'-内脂（2,3-二苄基丁内酯）的结构与其作为植物生长调节剂的活性之间的关系。合成了比天然二甲基金丝桃素 4 具有更高植物生长抑制活性的衍生物。具有 2-羟基-7-Z-烯结构的衍生物 42 对生菜幼苗的茎（IC=0.65mM）和根（IC=0.43mM）均显示出生长抑制活性。观察到了区域选择性活性。2,3-二羟基衍生物 24 对意大利黑麦草幼苗的茎（IC=0.36mM）和根（IC=0.13mM）均显示出最高的生长抑制活性。当 2,3-二羟基衍生物 24 中 3 位的羟基被氟原子取代时，其对意大利黑麦草幼苗根的活性与 24 相似。（2-羟基，4-氟）-衍生物 33 对意大利黑麦草幼苗的茎（IC=0.79mM）和根（IC=0.14mM）也显示出生长抑制活性。发现活性水平取决于两个羟基或羟基和芳香环上的氟原子的位置。还表明了木脂素-9,9'-内脂结构的重要性。
