Journal article

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

Kah Yean Lum, Aya C Taki, Robin B Gasser, Ian Tietjen, Merrick G Ekins, Jonathan M White, Russell S Addison, Sasha Hayes, James St John, Rohan A Davis



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, 1..

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Awarded by Australian Research Council (ARC)

Awarded by Canadian Institutes for Health Research

Awarded by New Frontiers in Research Fund-Explorations

Funding Acknowledgements

The authors acknowledge the Australian Research Council (ARC) for support towards NMR and MS equipment (grants LE0668477, LE140100119, and LE0237908). R.B.G.'s research is currently supported by the ARC, Yourgene Health and Melbourne Water Corporation. The HIV screening was supported by the Canadian Institutes for Health Research (CIHR PJT-153057) (I.T.), the New Frontiers in Research Fund-Explorations (NRFRE-2018-01386) (I.T.), and a Griffith University-Simon Fraser University Collaborative Travel Grant (I.T., R.A.D.). We gratefully acknowledge the Australian Institute for Marine Science (AIMS) for supply of the two crinoid samples reported in this study. These samples are part of the AIMS Bioresources Library, which has recently been added to the NatureBank biota repository, where they are available for biodiscovery research. We also thank M. Bryant from the Queensland Museum for curation of the crinoid sample. K.Y.L. would like to acknowledge Griffith University for the Ph.D. scholarships (GUIPRS and GUPRS).