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A series of seven unusual dimeric naphthylisoquinoline alkaloids was isolated from the leaves of the tropical liana  Ancistrocladus ealaensis  J. Léonard, named cyclombandakamine A (1), 1- epi -cyclombandakamine A (2), and cyclombandakamines A 3–7  (3–7). These alkaloids have a chemically thrilling structural array consisting of a twisted dihydrofuran-cyclohexenone-isochromene system. The 1′″-epimer of 4, cyclombandakamine A 1  (8), had previously been discovered in an unidentified  Ancistrocladus  species related to  A. ealaensis . Both lianas produce the potential parent precursor, mbandakamine A (9), but only  A. ealaensis  synthesizes the corresponding cyclized form, along with a broad series of slightly modified analogs. The challenging isolation required, besides multi-dimensional chromatography, the use of a pentafluorophenyl stationary phase. Featuring up to six stereocenters and two types of chiral axes, their structures were elucidated by means of 1D and 2D NMR, HRESIMS, in combination with oxidative chemical degradation experiments as well as chiroptical (electronic circular dichroism spectroscopy) and quantum chemical calculations. Compared to the ‘open-chain’ parent compound 9, these dimers displayed rather moderate antiplasmodial activities.

scientific reports

An Unusually Broad Series of Seven Cyclombandakamines, Bridged Dimeric Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus ealaensis