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*,刘飞基金项目:国家自然科学基金(31570359,31470425);江苏省社会发展项目(BE2016753);江苏省中国科学院植物研究所青年基金(SQ201402)。
作者简介:郭现翠(1991-),女,硕士研究生。联系人:罗金岳,教授,025-85427635,E-mail:luojinyue@;刘飞,助理研究员,025-84347159,liufeiseu@。
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:为深入研究和利用传统中药吴茱萸中的吲哚喹唑啉生物碱,本文以吴茱萸次碱为原料,%-%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、MR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 (Ishiyama))具有较明显的抑菌活性,其中N-苄基硫代吴茱萸次碱(Ⅳ4b)和N-(4-***苄基)-硫代吴茱萸次碱(Ⅳ4d)%%。通过细胞毒活性实验发现所合成的化合物(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)。本研究对吴茱萸生物碱的开发利用及新型植物源农药的开发具有一定的借鉴意义。
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,: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;
of Botany, Jiangsu Province and Chinese Academy of Sciences, Nanjing Botanical Garden -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 MR. The antifungal activity on nine plant pathogens of pounds (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 (Ishiyama)]. The inhibitory rates of N-benzyl sulfo-rutaecarpine (Ⅳb4b) and N-(4-methyl benzyl) sulfo-rutaecarpine (Ⅳ4d) were % and %, respectively. The rutaecarpine derivatives were found
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