别隐品碱衍生物的合成及其生物活性  

Synthesis and biological activities of alkaloids from allocryptopine

作　　者：李浩鹏 史晨燕 刘睿媛 耿会玲 LI Haopeng;SHI Chenyan;LIU Ruiyuan;GENG Huiling(School of Chemistry and Pharmcy,Northwest A&F University,Yangling,Shaanxi 712100,China)

机构地区：[1]西北农林科技大学化学与药学院,陕西杨凌712100

出　　处：《西北农林科技大学学报（自然科学版）》2018年第11期96-104,共9页Journal of Northwest A&F University(Natural Science Edition)

基　　金：国家自然科学基金项目(31572038);陕西省农业攻关项目(2016NY-130);陕西省博士后科学基金项目(2014-03)

摘　　要：【目的】测定别隐品碱化合物抗植物病原真菌和杀灭兔痒螨的活性,为后续结构优化和药品研发提供依据。【方法】以从博落回中分离的别隐品碱为原药,对其十元氮杂环进行结构修饰,合成了12种衍生物A1～A12,采用质谱(ESI-MS)、核磁共振谱(1 H NMR和13 C NMR)对其结构进行表征。以嘧菌酯为阳性对照,采用菌丝生长速率法,测定50μg/mL目标化合物对6种常见植物病原真菌(苹果腐烂病菌(Valsa mali)、番茄早疫病菌(Alternaria solani)、小麦赤霉病菌(Fusarium graminearum)、玉米弯孢病菌(Curvularia lunata)、马铃薯干腐病菌(Fusarium solani)、水稻稻瘟病菌(Pyricularia oryza))的体外抗菌活性;采用浸虫法检测5mg/mL目标化合物对兔痒螨(Psoroptes cuniculi)的体外杀灭活性。【结果】确认了12种别隐品碱衍生物的结构,它们对供试菌均具有不同程度的抑制活性,对兔痒螨具有一定的杀灭活性。其中,以化合物A11的抑菌活性和杀螨活性最高,其对苹果腐烂病菌的抑制率达73.28%,对兔痒螨的致死率达61.55%。【结论】原药别隐品碱十元氮杂环上的羰基被还原成羟基后,不仅提高了其抗菌活性和杀螨活性,同时也拓宽了其抗菌谱。【Objective】A series of allocryptopine derivatives were obtained by modifying the structure of allocryptopine and the antifungal activity against six phytopathogens and mortality against Psoroptes cuniculi were evaluated to provide basis for optimization and design of these chemicals.【Method】In this paper,twelve derivatives(A1-A12)were synthesized through structural modification on ten-membered N-heterocycle and they were characterized by ESI-MS,1H NMR,and 13 C NMR.Growth rate method was used to test antifungal activity of these compounds against six phytopathogens Valsa mali,Alternaria solani,Fusarium graminearum,Curvularia lunata,Fusarium solani,Fusarium graminearum at the concentration of 50μg/mL and the dipping-insect method was used to test the activity against P.cuniculi at the concentration of 5 mg/mL.【Result】Twelve derivatives were synthesized and their structures were confirmed by ESI-MS,1H NMR and 13 C NMR.The bioassay results showed that these compounds exhibited different inhibiting effects against all the tested phytopathogens.They also had certain poisonous activity against P.cuniculi.A11 had the highest inhibitory activity and acaricidal activity with the inhibition rate of 73.28%against Valsa mali and the lethality rate of 61.55%against P.cuniculi.【Conclusion】Reduction of carbonyl of ten-membered N-heterocycle to hydroxyl increased the antimicrobial activity and acaricidal activity and broadened the antifungal spectrum.

关 键 词：别隐品碱 结构修饰 抗菌活性 杀螨活性 

分 类 号：O621.2[理学—有机化学] S482.5[理学—化学]