A specific and potent inhibitor of brassinosteroid biosynthesis possessing a dioxolane ring
A specific and potent inhibitor of brassinosteroid biosynthesis possessing a dioxolane ring
复制标题
DOI：
10.1021/jf011716w
复制
发表时间：
2002-06-05
影响因子：
6.1
通讯作者：
Asami, T
中科院分区：
文献类型：
--
作者：
Sekimata, K;Han, SY;Asami, T
进行油菜素类固醇生物合成抑制剂的筛选，以发现诱导侏儒症的唑类衍生物，类似于拟南芥中的油菜素类固醇缺陷突变体，并且可以被油菜素类固醇拯救。通过筛选实验，选择丙环唑类杀菌剂作为油菜素内酯生物合成的潜在抑制剂，合成了具有最佳活性和选择性的丙环唑衍生物。通过检查水芹茎伸长来评价这些化合物的生物活性。在所测试的化合物中，2 RS，4 RS-1-[2-（4-三氟甲基苯基）-4-正丙基-1，3-二氧戊环-2-基甲基]-1H-1，2，4-三唑（12）显示出在光照下最有效的延迟水芹茎伸长的能力。化合物诱导的下胚轴矮化通过10 nM油菜素的共同应用而恢复，但不通过1 μ M赤霉素。这些结果表明，12应该影响油菜素类固醇的生物合成。12的效力和特异性大于先前报道的油菜素内酯生物合成抑制剂油菜唑。
Screening for brassinosteroid biosynthesis inhibitors was performed to find azole derivatives that induced dwarfism, to resemble brassinosteroid-deficient mutants in Arabidopsis, and which could be rescued by brassinosteroid. Through this screening experiment, propiconazole fungicide was selected as a likely inhibitor of brassinosteroid biosynthesis and, thus, propiconazole derivatives with optimized activity and selectivity were synthesized. The biological activity of these compounds was evaluated by examining cress stem elongation. Among the compounds tested, 2RS,4RS-1-[2-(4-trifluoromethylphenyl)-4-n-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole (12) showed the most potent capability to retard cress stem elongation in the light. The compound-induced hypocotyl dwarfism was restored by the coapplication of 10 nM brassinolide but not by 1 muM gibberellin. These results suggest that 12 should affect brassinosteroid biosynthesis. The potency and specificity of 12 were greater than those of brassinazole, a previously reported brassinosteroid biosynthesis inhibitor.