隐品碱衍生物的合成及其抗真菌活性

Synthesis and Antifungal Activity of Cryptopine Derivatives

[目的]以药用植物博落回中分离的隐品碱为原料,对其母核的十元氮杂环和苯环进行结构修饰,得到了11种隐品碱衍生物,对这些化合物结构进行表征后,考查了其体外抗真菌活性。[方法]先根据ESI-MS、1H NMR和13C NMR波谱数据确认了这些衍生物的结构;再以醚菌酯为阳性对照,在50 mg/L质量浓度下,采用菌丝生长速率法测定了合成的化合物对12种常见植物病原真菌的体外抑制活性。[结果]抑菌试验结果表明:大部分化合物对供试病原菌具有不同程度的抑制活性;其中化合物C8对苹果炭疽病菌的抑制活性最高,抑制率为44.3%。[结论]对目标化合物的结构及其抑菌活性进行初步分析,发现在隐品碱十元氮杂环上的13位引入羰基后,其抑菌活性会显著提高,这一研究为隐品碱类抗菌剂的开发提供了一定的理论基础。

[Aims] The cryptopine isolated from Macleaya cordata(Willd.) R. Br. was picked as the starting material.After modifying its ten-membered nitrogen heterocycle and phenyl ring, 11 types of derivatives of cryptopine were successfully afforded. Their antifungal activities in vitro were investigated on the basis of determining the chemical structure of all prepared compounds. [Methods] Firstly, the structures of synthesized compounds were characterized by the spectra of ESI-MS,1H NMR and 13C NMR data. Then, using kresoxim-methyl as positive control, the in vitro antifungal activity of the target compounds against 12 kinds of common phytopathogenic fungi was screened by hyphal linear growth rate method at the concentration of 50 mg/L. [Results] Most of the compounds have different degree of inhibitory activity on the tested fungi. Among them, compound C8 exhibited the highest inhibitory activity against Colletotrichum gloeosporioides with inhibition rate of 44.3%. [Conclusions] We analyzed the relationship between the structure and inhibitory activity of the target compounds. It was found that the antifungal activity of cryptopine significantly increased by introducing one carbonyl group into 13 position of the 10-membered nitrogen heterocycle.The research will provide a theoretical basis for the development of cryptopine antifungal agent.