Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines

Li, J; Seupel, R; Feineis, D; Mudogo, V; Kaiser, M; Brun, R; Brünnert, D; Chatterjee, M; Seo, E; Efferth, T; Bringmann, G

Journal article

Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines

Abstract:: Dioncophylline F (1), the first 5,8'-coupled dioncophyllaceous alkaloid (i.e., lacking an oxygen function at C-6 and possessing an R-configuration at C-3), was isolated from the recently described Congolese liana Ancistrocladus ileboensis. Two further, likewise Dioncophyllaceae-type, alkaloids, the dioncophyllines C2 (2) and D2 (3), were identified, along with the Ancistrocladaceae-type compound ancistrocladisine B (4), which is oxygenated at C-6 and S-configured at C-3. The structures of the new compounds were determined by spectroscopic, chemical, and chiroptical methods. The stereostructure of 1 was further confirmed by total synthesis. As a consequence of the lack of a methyl group ortho to their biaryl axes, both dioncophylline F (1) and the 7,8'-coupled dioncophylline D2 (3) occur as pairs of configurationally semistable and, thus, slowly interconverting atropo-diastereomers, whereas dioncophylline C2 (2), with its 5,1'-linkage, is configurationally stable at the axis. Eight further known naphthylisoquinolines were isolated from A. ileboensis, among them dioncophylline A (P-10), its 4'-O-demethyl analogue P-11, and 5'-O-methyldioncophylline D (7), which were found to display strong cytotoxic activities against multiple myeloma INA-6 cells (P-10 even stronger than the standard drug melphalan) and against drug-sensitive acute lymphoblastic CCRF-CEM leukemia cells and their multidrug-resistant subline, CEM/ADR5000. Moreover, the dioncophyllines 1, 3, and 7 showed high-and specific-activities against the malaria parasite Plasmodium falciparum.

Publication status:: Published

Peer review status:: Peer reviewed

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APA Style

Li, J., Seupel, R., Feineis, D., Mudogo, V., Kaiser, M., Brun, R., Brünnert, D., Chatterjee, M., Seo, E., Efferth, T., & Bringmann, G. (2017). Dioncophyllines C2, D2, and F and related naphthylisoquinoline alkaloids from the Congolese liana Ancistrocladus ileboensis with potent activities against Plasmodium falciparum and against multiple myeloma and leukemia cell lines. Journal of Natural Products, 80(2), 443–458.

MLA Style

Li, J., et al. “Dioncophyllines C2, D2, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus Ileboensis with Potent Activities against Plasmodium Falciparum and against Multiple Myeloma and Leukemia Cell Lines.” Journal of Natural Products, vol. 80, no. 2, American Chemical Society, 2017, pp. 443–58.

Chicago Style

Li, J, R Seupel, D Feineis, V Mudogo, M Kaiser, R Brun, D Brünnert, et al. 2017. “Dioncophyllines C2, D2, and F and Related Naphthylisoquinoline Alkaloids from the Congolese Liana Ancistrocladus Ileboensis with Potent Activities against Plasmodium Falciparum and against Multiple Myeloma and Leukemia Cell Lines.” Journal of Natural Products 80 (2): 443–58.
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