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 moderateFrom 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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Author details:Gerhard Bringmann, Joan Mutanyatta-Comar, Katja Maksimenka, John M. Wanjohi, Matthias HeydenreichORCiD, Reto Brun, Werner E. G. Müller, Martin Peter, Jacob O. Midiwo, Abiy YenesewORCiD
URN:urn:nbn:de:kobv:517-opus-42638
Publication series (Volume number):Zweitveröffentlichungen der Universität Potsdam : Mathematisch-Naturwissenschaftliche Reihe (paper 104)
Publication type:Postprint
Language:English
Publication year: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
DDC classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
License (German):License LogoKeine öffentliche Lizenz: Unter Urheberrechtsschutz
External remark:
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
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