State Key Laboratory of Elemento-Organic Chemistry, College of Chemistry, Frontiers Science Center for New Organic Matter, Nankai University, Tianjin 300071, China.
College of Basic Science, Tianjin Agricultural University, Tianjin 300384, China.
J Agric Food Chem. 2021 Dec 22;69(50):15123-15135. doi: 10.1021/acs.jafc.1c05792. Epub 2021 Dec 13.
Because gossypol and hemigossypol show antiviral activity but are structurally complex, we designed and synthesized a series of structurally simpler phthalide and coumarin derivatives. The phthalide derivatives were synthesized by opening the naphthalene ring of hemigossypol, and the coumarin derivatives were synthesized by ring-opening reactions of the phthalide derivatives with the goal of investigating the effect of the lactone ring size on bioactivity. The bioassay results showed that the two series of target compounds possessed moderate to good activities against tobacco mosaic virus, One of the compounds showed in vivo inactivation, curative, and protection activities of 50 ± 1, 53 ± 3, and 48 ± 2% at 500 mg/L, values which are higher than those of gossypol (32 ± 1, 35 ± 1, 29 ± 1%, respectively) and comparable to those of hemigossypol (55 ± 1, 49 ± 1, and 48 ± 1%, respectively) and the commercial antiviral agent ningnanmycin (56 ± 2, 54 ± 1, 58 ± 1%) at the same dose. Thus, this compound is a promising candidate for the development of new anti-plant-virus agents. In addition, most of the synthesized compounds showed broad-spectrum activity when tested against 14 kinds of phytopathogenic fungi and showed selectivity against , , and . Moreover, some of the compounds exhibited activity against larvae; the two most active compounds exhibited larvicidal activities (LC) of 4.10 and 5.47 mg/L, respectively. Further studies showed that these compounds also exhibited insecticidal activities against , , and larvae.
由于黄烷醇和半黄烷醇具有抗病毒活性，但结构复杂，我们设计并合成了一系列结构更简单的邻苯二甲酸酐和香豆素衍生物。邻苯二甲酸酐衍生物是通过对半黄烷醇的萘环进行开环合成的，香豆素衍生物是通过邻苯二甲酸酐衍生物与内酯环的开环反应合成的，目的是研究内酯环大小对生物活性的影响。生物测定结果表明，这两个系列的目标化合物对烟草花叶病毒具有中等至良好的活性。其中一种化合物在 500mg/L 时表现出 50±1%的体内失活、治疗和保护活性，分别高于黄烷醇（32±1%、35±1%、29±1%）和半黄烷醇（55±1%、49±1%、48±1%）以及商业抗病毒剂宁南霉素（56±2%、54±1%、58±1%）的相应值。因此，该化合物是开发新型植物抗病毒剂的有前途的候选物。此外，大多数合成化合物在测试对 14 种植物病原菌时表现出广谱活性，对 、 、 具有选择性。此外，一些化合物对 幼虫表现出活性；两种最活跃的化合物对 幼虫的杀虫活性（LC）分别为 4.10 和 5.47mg/L。进一步的研究表明，这些化合物对 、 、 幼虫也表现出杀虫活性。
