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Pyrroloquinoline derivatives from a Tongan specimen of the marine sponge Strongylodesma tongaensis

Taufa, Taitusi and Gordon, Rose M.A. and Hashmi, Muhammad Ali and Hira, Kainat and Miller, John H. and Lein, Matthias and Fromont, Jane and Northcote, Peter T. and Keyzers, R. A. (2019) Pyrroloquinoline derivatives from a Tongan specimen of the marine sponge Strongylodesma tongaensis. Tetrahedron Letters, 60 (28). pp. 1825-1829. ISSN 0040-4039

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    Abstract

    Pyrroloquinoline alkaloids are well known bioactive metabolites commonly found from latrunculiid sponges. Two new pyrroloquinoline alkaloids, 6-bromodamirone B (1) and makaluvamine W (2), were isolated from the Tongan sponge Strongylodesma tongaensis. Makaluvamine W (2) contains an oxazole moiety, which is rare in this large group of natural products, and is the first example of a pyrroloquinoline with nitrogen substitution at C-8. Both 1 and 2 lacked activity against a human promyelocytic leukaemia cell line (HL-60), supporting the premise that an intact iminoquinone moiety plays a key role in the cytotoxicity of this compound class. The chemotaxonomic impact of these makaluvamine-type compounds is also discussed.

    Item Type: Journal Article
    Subjects: Q Science > QD Chemistry
    Divisions: Faculty of Science, Technology and Environment (FSTE) > School of Biological and Chemical Sciences
    Depositing User: Dr. Taitusi Taufa
    Date Deposited: 01 Jul 2019 15:01
    Last Modified: 01 Jul 2019 15:01
    URI: http://repository.usp.ac.fj/id/eprint/11619
    UNSPECIFIED

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