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  • Comatulins A-E, Taurine-Conjugated Anthraquinones from the Australian Crinoid Comatula rotalaria

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    Accepted Manuscript (AM)
    Author(s)
    Lum, Kah Yean
    Taki, Aya C
    Gasser, Robin B
    Tietjen, Ian
    Ekins, Merrick G
    White, Jonathan M
    Addison, Russell S
    Hayes, Sasha
    St John, James
    Davis, Rohan A
    Griffith University Author(s)
    St John, James A.
    Davis, Rohan A.
    Year published
    2020
    Metadata
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    Abstract
    Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A–E (1–5), together with 11 known marine natural products (6–16). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7-dimethyl ether (8), is reported here. Compounds 1, 2, 6–13, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the ...
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    Chemical investigations of two specimens of the Australian crinoid Comatula rotalaria afforded five new taurine-conjugated anthraquinones, comatulins A–E (1–5), together with 11 known marine natural products (6–16). The chemical structures of all the compounds were elucidated by detailed spectroscopic and spectrometric data analysis. The first X-ray crystal structure of a crinoid-derived acyl anthraquinone, rhodocomatulin 5,7-dimethyl ether (8), is reported here. Compounds 1, 2, 6–13, and two additional naphthopyrone derivatives, 17 and 18, were evaluated for their ability to inhibit HIV-1 replication in vitro; none of the compounds were active at 100 μM. Furthermore, compounds 1, 2, 6–10, 14, 15, 17, and 18 were screened for nematocidal activity against exsheathed third-stage larvae of Hemonchus contortus, a highly pathogenic parasite nematode of ruminants. Compound 17, known as 6-methoxycomaparvin 5,8-dimethyl ether, showed an inhibitory effect on larval motility (IC50 = 30 μM) and development (IC50 = 31 μM) and induced the eviscerated (Evi) phenotype.
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    Journal Title
    Journal of Natural Products
    Volume
    83
    Issue
    6
    DOI
    https://doi.org/10.1021/acs.jnatprod.0c00267
    Copyright Statement
    This document is the Accepted Manuscript versionof a Published Work that appeared in final form in Journal of Natural Products, copyright 2020 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/acs.jnatprod.0c00267
    Subject
    Chemical sciences
    Biological sciences
    Biomedical and clinical sciences
    Science & Technology
    Life Sciences & Biomedicine
    Plant Sciences
    Chemistry, Medicinal
    Pharmacology & Pharmacy
    Publication URI
    http://hdl.handle.net/10072/396778
    Collection
    • Journal articles

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