Joziknipholones A and B : the First Dimeric Phenylanthraquinones, from the Roots of Bulbine frutescens

  • From the roots of the African plant Bulbine frutescens (Asphodelaceae), two unprecedented novel dimeric phenylanthraquinones, named joziknipholones A and B, possessing axial and centrochirality, were isolated, together with six known compounds. Structural elucidation of the new metabolites was achieved by spectroscopic and chiroptical methods, by reductive cleavage of the central bond between the monomeric phenylanthraquinone and -anthrone portions with sodium dithionite, and by quantum chemical CD calculations. Based on the recently revised absolute axial configuration of the parent phenylanthraquinones, knipholone and knipholone anthrone, the new dimers were attributed to possess the P-configuration (i.e., with the acetyl portions below the anthraquinone plane) at both axes in the case of joziknipholone A, whereas in joziknipholone B, the knipholone part was found to be M-configured. Joziknipholones A and B are active against the chloroquine resistant strain K1 of the malaria pathogen, Plasmodium falciparum, and show moderate activiFrom the roots of the African plant Bulbine frutescens (Asphodelaceae), two unprecedented novel dimeric phenylanthraquinones, named joziknipholones A and B, possessing axial and centrochirality, were isolated, together with six known compounds. Structural elucidation of the new metabolites was achieved by spectroscopic and chiroptical methods, by reductive cleavage of the central bond between the monomeric phenylanthraquinone and -anthrone portions with sodium dithionite, and by quantum chemical CD calculations. Based on the recently revised absolute axial configuration of the parent phenylanthraquinones, knipholone and knipholone anthrone, the new dimers were attributed to possess the P-configuration (i.e., with the acetyl portions below the anthraquinone plane) at both axes in the case of joziknipholone A, whereas in joziknipholone B, the knipholone part was found to be M-configured. Joziknipholones A and B are active against the chloroquine resistant strain K1 of the malaria pathogen, Plasmodium falciparum, and show moderate activity against murine leukemic lymphoma L5178y cells.show moreshow less

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Metadaten
Author:Gerhard Bringmann, Joan Mutanyatta-Comar, Katja Maksimenka, John M. Wanjohi, Matthias Heydenreich, Reto Brun, Werner E. G. Müller, Martin Peter, Jacob O. Midiwo, Abi Yenesew
URN:urn:nbn:de:kobv:517-opus-42638
Series (Serial Number):Postprints der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (paper 104)
Document Type:Postprint
Language:English
Date of Publication (online):2010/05/12
Year of Completion:2008
Publishing Institution:Universität Potsdam
Release Date:2010/05/12
Tag:antimalarial activity; chirality; joziknipholones; natural products; structure elucidation
Source:Chemistry - A European Journal 14 (2008) 5, S. 1420 - 1429, DOI 10.1002/chem.200701328
Organizational units:Mathematisch-Naturwissenschaftliche Fakultät / Institut für Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoKeine Nutzungslizenz vergeben - es gilt das deutsche Urheberrecht
Notes extern:
The original publication is available at www3.interscience.wiley.com:
Chemistry - A European Journal . - 14 (2008) Issue 5, p. 1420 - 1429
ISSN 0947-6539
DOI 10.1002/chem.200701328