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  • Lignans from the Australian Endemic Plant Austrobaileya scandens

    Author(s)
    Tran, Trong D
    Pham, Ngoc B
    Booth, Ron
    Forster, Paul I
    Quinn, Ronald J
    Griffith University Author(s)
    Quinn, Ronald J.
    Year published
    2016
    Metadata
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    Abstract
    The sole species of the vascular plant family Austrobaileyaceae, Austrobaileya scandens, is endemic to the tropical rainforest of northeastern Queensland, Australia. A single lead-like enhanced fraction of A. scandens showed potent inhibition against human prostate cancer PC3 cells. Chemical investigation of this plant resulted in the isolation of two new aryltetralin lignans, austrobailignans 8 and 9 (1 and 2), and the synthetic compound nicotlactone B (3), newly identified as a natural product together with nine known lignans (4–12). Their structures were established on the basis of spectroscopic analyses. Absolute ...
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    The sole species of the vascular plant family Austrobaileyaceae, Austrobaileya scandens, is endemic to the tropical rainforest of northeastern Queensland, Australia. A single lead-like enhanced fraction of A. scandens showed potent inhibition against human prostate cancer PC3 cells. Chemical investigation of this plant resulted in the isolation of two new aryltetralin lignans, austrobailignans 8 and 9 (1 and 2), and the synthetic compound nicotlactone B (3), newly identified as a natural product together with nine known lignans (4–12). Their structures were established on the basis of spectroscopic analyses. Absolute configurations of the new compounds were determined by quantum chemical electronic circular dichroism (ECD) calculations employing time-dependent density functional theory. The ECD calculations were also used to assign the absolute configuration of marphenol K (4) and revise the absolute configuration of kadsurindutin C (20). Ten out of the 12 isolated compounds inhibited the growth of PC3 cells with IC50 values ranging from micromolar to nanomolar. Marphenol A (5) was found for the first time to induce apoptosis and arrest the S cell cycle phase of PC3 cells.
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    Journal Title
    Journal of Natural Products
    Volume
    79
    Issue
    6
    DOI
    https://doi.org/10.1021/acs.jnatprod.5b00988
    Subject
    Chemical sciences
    Biological sciences
    Other biological sciences not elsewhere classified
    Biomedical and clinical sciences
    Publication URI
    http://hdl.handle.net/10072/100175
    Collection
    • Journal articles

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