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  • Thiaplakortones A-D: Antimalarial Thiazine Alkaloids from the Australian Marine Sponge Plakortis lita

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    Davis69267-Accepted.pdf (364.0Kb)
    File version
    Accepted Manuscript (AM)
    Author(s)
    Davis, Rohan A
    Duffy, Sandra
    Fletcher, Sabine
    Avery, Vicky M
    Quinn, Ronald J
    Griffith University Author(s)
    Quinn, Ronald J.
    Davis, Rohan A.
    Duffy, Sandra
    Avery, Vicky M.
    Fletcher, Sabine
    Year published
    2013
    Metadata
    Show full item record
    Abstract
    A high-throughput screening campaign using a prefractionated natural product library and an in vitro antimalarial assay identified active fractions derived from the Australian marine sponge Plakortis lita . Bioassay-guided fractionation of the CH2Cl2/CH3OH extract from P. lita resulted in the purification of four novel thiazine-derived alkaloids, thiaplakortones A-D (1-4). The chemical structures of 1-4 were determined following analysis of 1D/2D NMR and MS data. Comparison of the chiro-optical data for 3 and 4 with literature values of related N-methyltryptophan natural products was used to determine the absolute configuration ...
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    A high-throughput screening campaign using a prefractionated natural product library and an in vitro antimalarial assay identified active fractions derived from the Australian marine sponge Plakortis lita . Bioassay-guided fractionation of the CH2Cl2/CH3OH extract from P. lita resulted in the purification of four novel thiazine-derived alkaloids, thiaplakortones A-D (1-4). The chemical structures of 1-4 were determined following analysis of 1D/2D NMR and MS data. Comparison of the chiro-optical data for 3 and 4 with literature values of related N-methyltryptophan natural products was used to determine the absolute configuration for both thiaplakortones C and D as 11S. Compounds 1-4 displayed significant growth inhibition against chloroquine-sensitive (3D7) and chloroquine-resistant (Dd2) Plasmodium falciparum (IC50 values <651 nM) and only moderate cytotoxicity against HEK293 cells (IC50 values >3.9 卩. Thiaplakortone A (1) was the most active natural product, with IC50 values of 51 and 6.6 nM against 3D7 and Dd2 lines, respectively.
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    Journal Title
    Journal of Organic Chemistry
    Volume
    78
    Issue
    19
    DOI
    https://doi.org/10.1021/jo400988y
    Copyright Statement
    This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Organic Chemistry, copyright 2013 American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/jo400988y
    Subject
    Medicinal and biomolecular chemistry
    Medicinal and biomolecular chemistry not elsewhere classified
    Organic chemistry
    Publication URI
    http://hdl.handle.net/10072/56565
    Collection
    • Journal articles

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