Pan Le, Li Xiuzhuang, Jin Hui, Yang Xiaoyan, Qin Bo
Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China; Chemical Engineering College, Xinjiang Agricultural University, Urumqi 830052, People's Republic of China.
Key Laboratory of Chemistry of Northwestern Plant Resources of CAS and Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, People's Republic of China.
Microb Pathog. 2017 Mar;104:110-115. doi: 10.1016/j.micpath.2017.01.024. Epub 2017 Jan 12.
Umbelliferone was an important allelochemical with a wide spectrum bioactivity. In our previous study, C7 hydroxy in the backbone of umbelliferone was identified to be responsible for its phytotoxicity and the targeted modification of the above site could lead to the phytotoxicity loss. In view of this, a series of hydroxycoumarins and C7 O-substituted umbelliferone derivatives were efficiently synthesized to evaluate their antifungal activity against four phytopathogenic fungi. Most of them, as we predicted, exhibited improved fungicidal activity. The phytotoxicity of effective compounds was also assayed by Lactuca sativa to investigate their side effects on plant growth. Compounds 9 and 17 were identified to show strong antifungal activity with low phytotoxicity. A brief investigation on structure-activity relationships revealed that the modification at the C7 hydroxy of umbelliferone could be a promising way to enhance the antifungal activity with decreasing the phytotoxicity.
伞形酮是一种具有广泛生物活性的重要化感物质。在我们之前的研究中，已确定伞形酮主链上的C7羟基是其植物毒性的原因，对上述位点进行靶向修饰可导致植物毒性丧失。鉴于此，我们高效合成了一系列羟基香豆素和C7 O-取代的伞形酮衍生物，以评估它们对四种植物病原真菌的抗真菌活性。正如我们所预测的，它们中的大多数表现出了提高的杀菌活性。还通过生菜测定了有效化合物的植物毒性，以研究它们对植物生长的副作用。已确定化合物9和17具有较强的抗真菌活性且植物毒性较低。对构效关系的简要研究表明，对伞形酮的C7羟基进行修饰可能是一种在降低植物毒性的同时增强抗真菌活性的有前途的方法。
