Lombe Blaise Kimbadi, Feineis Doris, Mudogo Virima, Kaiser Marcel, Bringmann Gerhard
Institute of Organic Chemistry, University of Würzburg, Am Hubland, D-97074 Würzburg, Germany.
Faculté des Sciences, Université de Kinshasa, B.P. 202, Kinshasa XI, Democratic Republic of the Congo.
J Nat Prod. 2021 Apr 23;84(4):1335-1344. doi: 10.1021/acs.jnatprod.1c00063. Epub 2021 Apr 12.
Spirombandakamine A () is only the third known naphthylisoquinoline dimer with a spiro-fused novel molecular framework and the first such representative to possess a relative -configuration at the two chiral centers in both tetrahydroisoquinoline subunits. It was found in the leaves of a botanically as yet unidentified Congolese plant, which is morphologically closely related to the Central African taxon . Likewise isolated were the new cyclombandakamines A () and A (), which belong to another most recently discovered type of unusual oxygen-bridged naphthylisoquinoline dimers and two previously described "open-chain" analogues, mbandakamines C () and D (). The full absolute stereostructures of these compounds were assigned by combining spectroscopic, chemical, and chiroptical methods. Preliminary biomimetic investigations indicated that both spirombandakamine- and cyclombandakamine-type dimers result from the oxidation of their open-chain mbandakamine-type congeners. The new dimeric alkaloids - displayed potent growth-inhibitory activity against , the protozoal pathogen causing malaria, and moderate effects on , the parasite responsible for African sleeping sickness.
螺旋班达卡明A（）是已知的第三种具有螺稠合新型分子骨架的萘基异喹啉二聚体，也是第一种在两个四氢异喹啉亚基的两个手性中心均具有相对构型的此类代表物。它是在一种植物学上尚未鉴定的刚果植物的叶子中发现的，该植物在形态上与中非分类群密切相关。同样分离出的还有新的环班达卡明A（）和A（），它们属于另一种最近发现的不寻常的氧桥连萘基异喹啉二聚体类型，以及两种先前描述的“开链”类似物，班达卡明C（）和D（）。通过结合光谱、化学和手性光学方法确定了这些化合物的完整绝对立体结构。初步的仿生研究表明，螺旋班达卡明型和环班达卡明型二聚体均由其开链班达卡明型同系物氧化产生。新的二聚体生物碱 - 对引起疟疾的原生动物病原体 显示出强大的生长抑制活性，对导致非洲昏睡病的寄生虫 有中等程度的影响。
