School of Chemical Sciences , University of Auckland , 23 Symonds Street , Auckland 1142 , New Zealand.
The MacDiarmid Institute of Advanced Materials and Nanotechnology , New Zealand.
J Nat Prod. 2018 Dec 28;81(12):2630-2637. doi: 10.1021/acs.jnatprod.8b00416. Epub 2018 Nov 28.
1,4-Benzodioxane lignans are a class of bioactive compounds that have received much attention through the years. Herein research pertaining to both 1,4-benzodioxane flavonolignans and 1,4-benzodioxane neolignans is presented. A novel synthesis of both traditional 1,4-benzodioxane flavonolignans and 3-deoxyflavonolignans is described. The antiviral and cytotoxic activities of 1,4-benzodioxane neolignans were then investigated; eusiderins A, B, G, and M, deallyl eusiderin A, and nitidanin, which contain the 1,4-benzodioxane motif but lack the chromanone motif found in the known antiviral flavonolignans, were tested. Notably, it was found that all eusiderin 1,4-benzodioxane neolignans exhibited greater antiviral activity than the potent and well-known silybin flavonolignans. While most modifications of the C-1' side chain did not significantly alter the cytotoxicity or antiviral activity, eusiderin M and nitidanin, which contain an allylic alcohol side chain, had lower cytotoxicity. All the eusiderins had similar antiviral activities, with eusiderin B having the best selectivity index. These results show that the chromanone moiety of the flavonolignans is not essential for bioactivity.
1,4-苯并二恶烷木脂素是一类生物活性化合物，多年来一直受到广泛关注。本文介绍了 1,4-苯并二恶烷黄酮木脂素和 1,4-苯并二恶烷新木脂素的研究。描述了传统的 1,4-苯并二恶烷黄酮木脂素和 3-脱氧黄酮木脂素的新合成方法。然后研究了 1,4-苯并二恶烷新木脂素的抗病毒和细胞毒性活性；对含有 1,4-苯并二恶烷母核但缺乏已知抗病毒黄酮木脂素中含有的色满酮母核的 eusiderins A、B、G 和 M、deallyl eusiderin A 和 nitidanin 进行了测试。值得注意的是，发现所有 eusiderin 1,4-苯并二恶烷新木脂素的抗病毒活性均强于强效且知名的水飞蓟宾黄酮木脂素。虽然 C-1'侧链的大多数修饰并未显著改变细胞毒性或抗病毒活性，但含有烯丙醇侧链的 eusiderin M 和 nitidanin 的细胞毒性较低。所有 eusiderin 均具有相似的抗病毒活性，其中 eusiderin B 的选择性指数最佳。这些结果表明，黄酮木脂素的色满酮部分对于生物活性并非必不可少。
