Institute of Natural Product Chemistry, Zhongkai University of Agriculture and Engineering, Guangzhou, Guangdong, 510225, China.
Department of Chemical and Biochemical Engineering, Western University, London, Ontario, N6A5B9, Canada.
Sci Rep. 2018 Oct 24;8(1):15686. doi: 10.1038/s41598-018-33908-8.
Matrine is a traditional Chinese medicine and botanical pesticide with broad biological activities, including pharmacological and agricultural activities. In present work, two matrine derivatives have been successfully synthesized via introducing indole and cyclohexylamino to 13 position of matrine, respectively, with sophocarpine as starting material, and structurally characterized via infrared spectroscopy(IR), MS, 1 H NMR, 13 C NMR and X-ray crystal diffraction. The results of the in vitro biological activity tests showed that these two matrine derivatives exhibited even better activities against human cancer cells Hela229 and insect cell line Sf9 from Spodoptera frugiperda (J. E. Smith) than that of parent matrine, suggesting that the heterocyclic or cyclic group can dramatically increase the biological activity of matrine. It is worth to mention that 13-indole-matrine could possibly inhibit the growth of insect cells or human cancer cells by inducing cell apoptosis. The results of the present study provide useful information for further structural modifications of these compounds and for exploring new, potent anti-cancer agents and environment friendly pesticides.
苦参碱是一种传统的中药和植物性农药，具有广泛的生物活性，包括药理学和农业学活性。在本工作中，以苦参碱为起始原料，通过在 13 位引入吲哚和环己基氨基，成功合成了两种苦参碱衍生物，并通过红外光谱（IR）、质谱（MS）、1H 核磁共振（1H NMR）、13C 核磁共振（13C NMR）和 X 射线单晶衍射对其结构进行了表征。体外生物活性测试结果表明，这两种苦参碱衍生物对人宫颈癌细胞 Hela229 和昆虫细胞 Sf9 （Spodoptera frugiperda （J. E. Smith））的活性均优于母体苦参碱，表明杂环或环基团可以显著提高苦参碱的生物活性。值得一提的是，13-吲哚-苦参碱可能通过诱导细胞凋亡来抑制昆虫细胞或人癌细胞的生长。本研究结果为进一步对这些化合物进行结构修饰以及探索新的、有效的抗癌药物和环境友好型农药提供了有用信息。
