edoc

Antiprotozoal dimeric naphthylisoquinolines, mbandakamines B3 and B4, and related 5,80'-coupled monomeric alkaloids, ikelacongolines A-D, from a Congolese Ancistrocladus liana

Mufusama, J. P. and Feineis, D. and Mudodo, V. and Kaiser, M. and Brun, R. and Bringmann, G.. (2019) Antiprotozoal dimeric naphthylisoquinolines, mbandakamines B3 and B4, and related 5,80'-coupled monomeric alkaloids, ikelacongolines A-D, from a Congolese Ancistrocladus liana. RSC advances, 9 (21). pp. 12034-12046.

[img] PDF - Published Version
Available under License CC BY-NC (Attribution-NonCommercial).

1113Kb

Official URL: https://edoc.unibas.ch/70437/

Downloads: Statistics Overview

Abstract

From the leaves of a botanically and phytochemically as yet unexplored Ancistrocladus liana discovered in the rainforests of the Central region of the Democratic Republic of the Congo in the vicinity of the town of Ikela, six new naphthylisoquinoline alkaloids were isolated, viz., two constitutionally unsymmetric dimers, the mbandakamines B3 (3) and B4 (4), and four related 5,8′-linked monomeric alkaloids, named ikelacongolines A–D (5a, 5b, 6, and 7). The dimers 3 and 4 are structurally unusual quateraryls comprising two 5,8′-coupled monomers linked via a sterically strongly constrained 6′,1′′-connection between their naphthalene units. These compounds contain seven elements of chirality, four stereogenic centers and three consecutive chiral axes. They were identified along with two known related compounds, the mbandakamines A (1) and B2 (2), which had so far only been detected in two Ancistrocladus species indigenous to the Northwestern Congo Basin. In addition, five known monomeric alkaloids, previously found in related Central African Ancistrocladus species, were isolated from the here investigated Congolese liana, three of them belonging to the subclass of 5,8′-coupled naphthylisoquinoline alkaloids, whereas two compounds exhibited a less frequently occurring 7,8′-biaryl linkage. The stereostructures of the new alkaloids were established by spectroscopic (in particular HRESIMS, 1D and 2D NMR), chemical (oxidative degradation), and chiroptical (electronic circular dichroism) methods. The mbandakamines B3 (3) and B4 (4) displayed pronounced activities in vitro against the malaria parasite Plasmodium falciparum and the pathogen of African sleeping sickness, Trypanosoma brucei rhodesiense.
Faculties and Departments: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 and Brun, Reto
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:Royal Society of Chemistry
ISSN:2046-2069
Note:Publication type according to Uni Basel Research Database: Journal article
Language:English
Identification Number:
edoc DOI:
Last Modified:15 May 2019 08:31
Deposited On:15 May 2019 08:31

Repository Staff Only: item control page