Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.
Chemistry. 2010 Apr 12;16(14):4206-16. doi: 10.1002/chem.200903247.
Five novel dimeric naphthylisoquinoline alkaloids, shuangancistrotectorines A (3 a), B (3 b), C (4), D (5 a), and E (5 b), have been isolated from the twigs of the Chinese plant Ancistrocladus tectorius. Their absolute stereostructures were determined by spectroscopic and chiroptical methods in combination with quantum chemical CD calculations. In contrast to all other known dimeric naphthylisoquinoline alkaloids, in which the central binaphthalene axis is 6',6''-coupled and thus not rotationally hindered, the dimers described here are linked via the sterically more hindered 3',3''- or 1',1''-positions of the naphthalene units. They are thus the first such dimers-and even the very first natural products at all-that have three consecutive stereogenic axes. Hence, including the stereogenic centers, they have up to seven stereogenic units in total. Some of the compounds, in particular shuangancistrotectorines A, B, and D (3 a, 3 b, and 5 a) exhibit very good, and specific, antiplasmodial activities.
双岸藤定酯素 A（3a）、B（3b）、C（4）、D（5a）和 E（5b）。通过光谱和手性光学方法结合量子化学 CD 计算确定了它们的绝对立体结构。与所有其他已知的二聚萘基异喹啉生物碱不同，这些生物碱的中心联萘轴是 6'，6''-偶联的，因此不受旋转阻碍，而这里描述的二聚体通过萘基单元的空间位阻更大的 3'，3''-或 1'，1''-位置连接。因此，它们是第一个具有三个连续的手性轴的此类二聚体，甚至是第一个天然产物。因此，它们总共具有多达七个手性单元。其中一些化合物，特别是双岸藤定酯素 A、B 和 D（3a、3b 和 5a）表现出非常好的、特异性的抗疟活性。
