article · Organic Letters
Two new natural compounds, named cyclombandakamines A1 and A2, have been isolated from the leaves of an unidentified Ancistrocladus liana collected in the Congo. These molecules represent the first discovered oxygen-bridged dimeric naphthylisoquinoline alkaloids. Their chemical architecture contains an unprecedented pyrane-cyclohexenone-dihydrofuran sequence, along with six stereocentres and two chiral axes. Detailed structural configurations were established using spectroscopic, chemical, and chiroptical methods combined with density functional theory calculations. The alkaloids appear to be generated through a cascade of oxidative cyclisation reactions from open-chain dimeric precursors. In biological evaluations, both compounds demonstrated significant antiprotozoal activities, marking them as structurally unique natural products with potential bioactivity against protozoan organisms.
Protozoan infections continue to pose major global health challenges, necessitating the discovery of novel chemical classes with antiparasitic potential. The identification of entirely new structural frameworks from Central African flora enriches natural product chemistry. Characterising these intricate molecular architectures aids researchers in understanding complex plant biosynthesis pathways and provides novel natural scaffolds that could inform the discovery of future antiprotozoal treatments.
The demonstrated antiprotozoal activity points toward potential applications in antiparasitic drug discovery, which may interest pharmaceutical developers and medicinal chemistry researchers. The research represents an early discovery-stage finding based purely on natural product isolation and characterisation. Extensive preclinical testing, safety profiling, and chemical synthesis or supply optimisation would be necessary before these molecules or their derivatives could move toward formal therapeutic development.
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Cyclombandakamines A<sub>1</sub> (1) and A<sub>2</sub> (2), both with an unprecedented pyrane-cyclohexenone-dihydrofuran sequence and six stereocenters and two chiral axes, are the first oxygen-bridged dimeric naphthylisoquinoline alkaloids. They were isolated from the leaves of an as yet unidentified Congolese Ancistrocladus species. Their stereostructures were established by spectroscopic, chemical, and chiroptical methods in combination with DFT and TDDFT calculations. They apparently originate from a cascade of oxidative cyclization reactions of "open-chain" naphthylisoquinoline dimers and exhibit significant antiprotozoal activities.
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DOI: 10.1021/acs.orglett.7b00209
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