异黄烯衍生物的合成及其抑菌活性  

Synthesis and Antifungal Activities of Isoflavenes Derivatives

作　　者：林晋雨 何桥[1] 王斌 杨银华 杨春平[1] 陈华保[1] 乐贵洲 LIN Jinyu;HE Qiao;WANG Bin;YANG Yinhua;YANG Chunping;CHEN Huabao;YUE Guizhou(College of Agronomy,Sichuan Agricultural University,Chengdu 611130,China;College of Sciences,Sichuan Agricultural University,Chengdu 611130,China)

机构地区：[1]四川农业大学农学院,四川成都611130 [2]四川农业大学理学院,四川成都611130

出　　处：《合成化学》2022年第11期841-847,共7页Chinese Journal of Synthetic Chemistry

基　　金：国家重点研发项目(2019YFD1002100,2018YFD0200500);四川省科技厅项目(2020YFH0129);四川省重大科技项目(2017NZDZX0003)。

摘　　要：光甘草定(Glabridin)作为光果甘草(Glycyrrhiza glabra L.)中主要异黄酮类活性成分之一,对多种植物病原菌具有明显的抑菌活性。基于光甘草定的结构,对其进行衍生化,有望开发出新型植物源农药。本文以邻羟基苯甲醇为起始原料,通过亲核取代、季鏻盐化和分子内维蒂希反应3步反应合成了12个3-芳基异黄烯衍生物(5a~5l),其结构经^(1)H NMR、^(13)C NMR和MS确证。采用菌丝生长速率抑制法测试了目标化合物对草莓灰霉病菌、西瓜枯萎病菌、马铃薯早疫病菌和烟草赤星病菌的抑制活性。结果表明:化合物5k对草莓灰霉病菌抑制活性较强(抑制率68.4%);化合物5g对马铃薯早疫病菌的抑制率(85.0%)明显高于光甘草定(61.9%);化合物5j对多种真菌病原体均表现出一定的抑制活性。Glabridin is one of the main isoflavones active constituents of Glycyrrhiza glabra L.,which can inhibit the growth of many pathogenic fungi,so it is expected to develop new botanical pesticides based on its structure.In this paper,twelve 3-aryl isoflavenes derivatives 5a~5l were synthesized by three-step reactions of nucleophilic substitution,quaternary phosphonium salts and intramolecular Wit-tig reaction using o-hydroxybenzyl alcohol as initial reagent and their structures were characterized by ^(1)H NMR,^(13)C NMR and MS.Further,mycelial growth inhibition assay was used to study whether these target compounds have anti-fungus activity against Botrytis cinerea,Fusarium graminearum,Alternaria solani and Alternaria alternate.Results showed that,compound 5k has higher efficacy against B.cine-rea(68.4%).Compared with glabridin(61.9%),compound 5g has higher antifungal activity against A.solani(85.0%).Moreover compound 5j has evident antifungal activities against fungal pathogens.

关 键 词：光甘草定 异黄烯 合成 亲核取代 季鏻盐化 维蒂希反应 抑菌活性 

分 类 号：O621.2[理学—有机化学]