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  • Grandisines C - G, Indolizidine Alkaloids from the Australian Rainforest Tree Elaeocarpus grandis

    Author(s)
    Katavic, Peter L
    Venables, Debra A
    Forster, Paul I
    Guymer, Gordon
    Carroll, Anthony R
    Griffith University Author(s)
    Carroll, Anthony R.
    Year published
    2006
    Metadata
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    Abstract
    Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4 - 8), and one known indolizidine alkaloid, (-)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (-)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an ...
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    Five new indolizidine alkaloids, grandisines C, D, E, F, and G (4 - 8), and one known indolizidine alkaloid, (-)-isoelaeocarpiline (3), were isolated from the leaves of Elaeocarpus grandis and their structures determined by 1D and 2D NMR spectroscopy. Grandisine C (4) is isomeric with the known compound rudrakine (1). The absolute configuration of grandisine D (5) was deduced by its conversion to (-)-isoelaeocarpiline. Grandisine E (6) contains a novel tetracyclic ring system. Grandisine F (7) is the 14-amino analogue of grandisine C. Grandisine G (8) contains the novel combination of a piperidine attached to an indolizidine. Grandisines C, D, F, and G and (-)-isoelaeocarpiline showed receptor binding affinity for the human d-opioid receptor with IC50 values of 14.6, 1.65, 1.55, 75.4, and 9.9 uM, respectively.
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    Journal Title
    Journal of Natural Products
    Volume
    69
    Publisher URI
    http://pubs.acs.org/journal/jnprdf
    DOI
    https://doi.org/10.1021/np060179c
    Subject
    Chemical sciences
    Biological sciences
    Biomedical and clinical sciences
    Publication URI
    http://hdl.handle.net/10072/14402
    Collection
    • Journal articles

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