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Mbandakamine-type naphthylisoquinoline dimers and related alkaloids from the central African liana ancistrocladus ealaensis with antiparasitic and antileukemic activities
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
ID
4482084
Author(s)
Tshitenge, Dieudonné Tshitenge; Feineis, Doris; Mudogo, Virima; Kaiser, Marcel; Brun, Reto; Seo, Ean-Jeong; Efferth, Thomas; Bringmann, Gerhard
Mbandakamine-type naphthylisoquinoline dimers and related alkaloids from the central African liana ancistrocladus ealaensis with antiparasitic and antileukemic activities
Journal
Journal of natural products
Volume
81
Number
4
Pages / Article-Number
918-933
Abstract
Four new dimeric naphthylisoquinoline alkaloids, michellamine A; 5; (2) and mbandakamines C-E (4-6), were isolated from the Congolese plant Ancistrocladus ealaensis, along with the known dimer mbandakamine A (3). They represent constitutionally unsymmetric dimers, each consisting of two 5,8'-coupled naphthylisoquinoline monomers. While the molecular halves of michellamine A; 5; (2) are linked via C-6' of both of the naphthalene moieties, i.e., via the least-hindered positions, so that the central biaryl axis is configurationally unstable and not an additional element of chirality, the mbandakamines 3-6 possess three consecutive stereogenic axes. Their monomeric units are linked through an unprecedented 6',1″-coupling in the binaphthalene core, leading to a high steric load, since the central axis is located in one of the peri-positions, neighboring one of the outer axes. In addition, four new 5,8'-coupled monomeric naphthylisoquinolines, viz., ancistroealaines C-F (7-10), were identified, along with four "naphthalene-devoid" tetra- and dihydroisoquinolines, named ealaines A-D (11-14). The new mbandakamines C (4) and D (5) showed pronounced activities against the malaria parasite Plasmodium falciparum, and they were likewise found to display strong cytotoxic activities against human leukemia (CCRF-CEM) and multi-drug-resistant tumor cells (CEM/ADR5000).
