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  • Synthesis and antimalarial evaluation of a screening library based on a tetrahydroanthraquinone natural product scaffold

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    Author(s)
    Choomuenwai, Vanida
    Andrews, Katherine T
    Davis, Rohan A
    Griffith University Author(s)
    Andrews, Katherine T.
    Davis, Rohan A.
    Year published
    2012
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    Abstract
    As part of a research program aimed at discovering new antimalarial leads from Australian macrofungi a unique fungi-derived prefractionated library was screened against a chloroquine-sensitive Plasmodium falciparum line (3D7) using a radiometric growth inhibition assay. A library fraction derived from a Cortinarius species displayed promising antimalarial activity. UV-guided fractionation on the CH2Cl2/MeOH extract from this fungus resulted in the isolation of four known compounds: (1S,3R)-austrocortirubin (1), (1S,3S)-austrocortirubin (2), 1-deoxyaustrocortirubin (3), and austrocortinin (4). Compound 2 was used as a natural ...
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    As part of a research program aimed at discovering new antimalarial leads from Australian macrofungi a unique fungi-derived prefractionated library was screened against a chloroquine-sensitive Plasmodium falciparum line (3D7) using a radiometric growth inhibition assay. A library fraction derived from a Cortinarius species displayed promising antimalarial activity. UV-guided fractionation on the CH2Cl2/MeOH extract from this fungus resulted in the isolation of four known compounds: (1S,3R)-austrocortirubin (1), (1S,3S)-austrocortirubin (2), 1-deoxyaustrocortirubin (3), and austrocortinin (4). Compound 2 was used as a natural product scaffold in the parallel solution-phase synthesis of a small library of N-substituted tetrahydroanthraquinones (5-15). All compounds (1-15) were tested in vitro against P. falciparum 3D7 parasites and (1S,3S)-austrocortirubin (2), the major fungal constituent, was shown to be the most active compound with an IC50 of 1.9 卮 This compound displayed moderate cytotoxicity against neonatal foreskin fibroblast (NFF) cells with an IC50 of 15.6 卮
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    Journal Title
    Bioorganic & Medicinal Chemistry
    Volume
    20
    Issue
    24
    DOI
    https://doi.org/10.1016/j.bmc.2012.09.052
    Copyright Statement
    © 2012 Elsevier. This is the author-manuscript version of this paper. Reproduced in accordance with the copyright policy of the publisher. Please refer to the journal's website for access to the definitive, published version.
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Infectious agents
    Pharmacology and pharmaceutical sciences
    Biochemistry and cell biology
    Publication URI
    http://hdl.handle.net/10072/51656
    Collection
    • Journal articles

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