吴茱萸次碱衍生物的合成及抑菌活性.doc

吴茱萸次碱衍生物的合成及抑菌活性 郭现翠1，王奇志2，徐曙2，单宇2，印敏2，冯煦2，罗金岳1*，刘飞(2* （1. 南京林业大学化学工程学院，江苏南京 210037；2. 江苏省中国科学院植物研究所（南京中山植物园），江苏南京 210014） 摘要：以吴茱萸次碱为原料，通过硫代反应等以54.5%-87.6%的收率合成了硫代吴茱萸次碱及其5种N-取代衍生物（Ⅱ、Ⅳa~e），采用HRMS、FTIR、1HNMR和13CNMR对产物进行了结构表征；分析了10 μg/mL的样品对9种植物病原菌的抑菌活性。结果表明：合成的六种化合物（Ⅱ、Ⅳa~e）对植物病原真菌几乎没有抑制作用，化合物Ⅳa、Ⅳb及Ⅳd对细菌（水稻白叶枯病菌，Xanthomonas?oryzae?pv.oryzae (Ishiyama)）具有较明显的抑菌活性，其中N-苄基硫代吴茱萸次碱（Ⅳb）和N-(4-甲基苄基)-硫代吴茱萸次碱（Ⅳd）的抑制率分别为81.84%和59.95%。通过细胞毒活性实验发现合成的化合物（Ⅱ、Ⅳa~e）对人体正常细胞（人肺成纤维细胞，HFL1）几乎没有毒性（IC50 80 μmol/L）。 关键词：吴茱萸次碱；硫代吴茱萸次碱；抑菌活性；农药 中图分类号：TQ455. 47，O629.3文献标识码：A Synthesis and Antifungal Activity of Rutaecarpine Derivatives GUOXian-cui1, WANG Qi-zhi2, XU Shu2, SHAN Yu2, YIN Min2, FENG Xu2, LUO Jin-yue1*, LIU Fei2* (1. College of Chemical Engineering, Nanjing Forestry University, Nanjing 210037, China; 2.Institute of Botany, Jiangsu Province and Chinese Academy of Sciences, Nanjing Botanical Garden Mem.SunYat-Sen, Nanjing 210014, China) Abstract: In order to study and develop the indole quinazoline alkaloid of the traditional Chinese medicine evodia, the thiorutaecarpine and five N-substituted derivatives were synthesized from rutaecarpine by thionation. The structures of the products were confirmed by HPLC-HRMS, IR, 1HNMR and 13CNMR. The antifungal activity on nine plant pathogens of the compounds (Ⅱ and Ⅳa~e, 10(μg/mL) was analyzed, and it was found that there was almost no inhibitory effect on the plant pathogenic fungi, and N-substituted thiorutaecarpine (Ⅳa, Ⅳb and Ⅳd) had obvious antifungal activity against bacteria [Xanthomonas?oryzae?pv.oryzae (Ishiyama)]. The inhibitory rates of N-benzyl sulfo-rutaecarpine (Ⅳb) and N-(4-methyl benzyl) sulfo-rutaecarpine (Ⅳd) were 81.84% and 59.95%, respectively. The rutaecarpine derivatives were found to be almost non-toxic (IC50 80 μmol/L) to human normal cells (HFL1) by cytotoxicity assay. Key words: rutaecarpine; sulfo-rutaecarpine; antifungal activity; pesticides Foundation items: National?Natural?Science?Foundation?of?China?(No:?3157035