Department of Chemistry, Ahmadu Bello University, Zaria, Nigeria.
Institute of Organic Chemistry, University of Würzburg, Würzburg, Germany.
Nat Prod Res. 2024 Aug;38(15):2614-2618. doi: 10.1080/14786419.2023.2194648. Epub 2023 Mar 29.
Ancistrobrevinium A () is the first -methylated and non-hydrogenated, and thus cationic naphthylisoquinoline alkaloid. It was discovered in the root bark extract of the phytochemically productive West African liana (Ancistrocladaceae). Its constitution was elucidated by HR-ESI-MS and 1D and 2D NMR. Due to the steric hindrance in the proximity of the linkage between the naphthalene and isoquinoline parts, the biaryl axis is rotationally hindered. It thus constitutes a stable element of chirality - the only one in the new alkaloid since, different from most other naphthylisoquinoline alkaloids, it has no stereogenic centers. The axial configuration of was assigned by electronic circular dichroism (ECD) investigations, which gave a positive couplet, indicating a 'positive chirality', here corresponding to a -configuration. Ancistrobrevinium A () showed a weak cytotoxic activity against A549 lung cancer cells (IC = 50.6 μM).
安斯屈布灵因 A（）是第一个甲基化和非氢化的阳离子萘基异喹啉生物碱。它是在具有化学生产能力的西非藤本植物（Ancistrocladaceae）的根皮提取物中发现的。其结构通过高分辨电喷雾质谱（HR-ESI-MS）和 1D 和 2D NMR 阐明。由于萘和异喹啉部分之间连接的空间位阻，双芳基轴受到阻碍。因此，它构成了手性的稳定元素 - 这是新生物碱中唯一的一个，因为与大多数其他萘基异喹啉生物碱不同，它没有手性中心。通过电子圆二色性（ECD）研究确定了的轴向构型，产生了一个正偶合，表明“正手性”，这里对应于 -构型。安斯屈布灵因 A（）对 A549 肺癌细胞表现出较弱的细胞毒性（IC = 50.6 μM）。
