State Key Laboratory of Elemento-Organic Chemistry, Research Institute of Elemento-Organic Chemistry, Collaborative Innovation Center of Chemical Science and Engineering (Tianjin), Nankai University , Tianjin 300071, China.
Tianjin Key Laboratory of Structure and Performance for Functional Molecules, Key Laboratory of Inorganic-Organic Hybrid Functional Materials Chemistry (Tianjin Normal University), Ministry of Education, College of Chemistry, Tianjin Normal University , Tianjin 300387, China.
J Agric Food Chem. 2016 Jun 1;64(21):4264-72. doi: 10.1021/acs.jafc.6b01415. Epub 2016 May 19.
Marine natural products polycarpine, polycarpaurines A and C, and their derivatives were designed, synthesized, and characterized on the basis of (1)H NMR and mass spectroscopy. The antiviral and antiphytopathogenic fungus activities of these alkaloids were first evaluated. Polycarpine derivative 1g displayed excellent in vivo antiviral activity against TMV (inactivation inhibitory effect, 57%/500 μg mL(-1) and 19%/100 μg mL(-1); curative inhibitory effect, 62%/500 μg mL(-1) and 23%/100 μg mL(-1); and protection inhibitory effect, 56%/500 μg mL(-1) and 29%/100 μg mL(-1)), which is evidently higher than the activity of ribavirin (inactivation inhibitory effect, 37%/500 μg mL(-1) and 9%/100 μg mL(-1); curative inhibitory effect, 36%/500 μg mL(-1) and 13%/100 μg mL(-1); and protection inhibitory effect, 39%/500 μg mL(-1) and 17%/100 μg mL(-1)), thus emerging as a new lead compound for antiviral research against TMV. Fungicidal testing in vitro showed that most of the compounds displayed good fungicidal activity against plant pathogenic fungi. Further in vivo fungicidal testing indicated that compounds 6a, 6f, and 8a-c displayed good fungicidal activity. Current results provide support for the development of polycarpine alkaloids as novel agrochemicals.
基于(1)H NMR 和质谱学,设计、合成并表征了海洋天然产物多卡宾、多卡宾碱 A 和 C 及其衍生物。首次评价了这些生物碱的抗病毒和抗植物病原真菌活性。多卡宾衍生物 1g 表现出优异的体内抗 TMV 活性(失活抑制作用,57%/500 μg mL(-1) 和 19%/100 μg mL(-1);治疗抑制作用,62%/500 μg mL(-1) 和 23%/100 μg mL(-1);保护抑制作用,56%/500 μg mL(-1) 和 29%/100 μg mL(-1)),明显高于利巴韦林的活性(失活抑制作用,37%/500 μg mL(-1) 和 9%/100 μg mL(-1);治疗抑制作用,36%/500 μg mL(-1) 和 13%/100 μg mL(-1);保护抑制作用,39%/500 μg mL(-1) 和 17%/100 μg mL(-1)),因此成为抗病毒研究抗 TMV 的新先导化合物。体外杀菌试验表明,大多数化合物对植物病原真菌具有良好的杀菌活性。进一步的体内杀菌试验表明,化合物 6a、6f 和 8a-c 具有良好的杀菌活性。目前的结果为多卡宾生物碱作为新型农用化学品的开发提供了支持。