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Spirombandakamine A3 and cyclombandakamines A8 and A9, polycyclic naphthylisoquinoline dimers, with antiprotozoal activity, from a Congolese Ancistrocladus plant

Lombe, B. K. and Feineis, D. and Mudogo, V. and Kaiser, M. and Bringmann, G.. (2021) Spirombandakamine A3 and cyclombandakamines A8 and A9, polycyclic naphthylisoquinoline dimers, with antiprotozoal activity, from a Congolese Ancistrocladus plant. Journal of natural products, 84 (4). pp. 1335-1344.

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Official URL: https://edoc.unibas.ch/89159/

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Abstract

Spirombandakamine A3 (7) is only the third known naphthylisoquinoline dimer with a spiro-fused novel molecular framework and the first such representative to possess a relative trans-configuration at the two chiral centers in both tetrahydroisoquinoline subunits. It was found in the leaves of a botanically as yet unidentified Congolese Ancistrocladus plant, which is morphologically closely related to the Central African taxon Ancistrocladus ealaensis. Likewise isolated were the new cyclombandakamines A8 (8) and A9 (9), which belong to another most recently discovered type of unusual oxygen-bridged naphthylisoquinoline dimers and two previously described "open-chain" analogues, mbandakamines C (10) and D (11). 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 7-9 displayed potent growth-inhibitory activity against Plasmodium falciparum, the protozoal pathogen causing malaria, and moderate effects on Trypanosoma brucei rhodesiense, the parasite responsible for African sleeping sickness.
Faculties and Departments:09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH)
09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser)
UniBasel Contributors:Kaiser, Marcel
Item Type:Article, refereed
Article Subtype:Research Article
ISSN:0163-3864
Note:Publication type according to Uni Basel Research Database: Journal article
Identification Number:
Last Modified:20 Dec 2022 12:06
Deposited On:20 Dec 2022 12:06

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