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  • Lepadins F-H. New cis-Decahydroquinoline Alkaloids from the Australian Ascidian, Aplidium tabascum

    Author(s)
    Davis, RA
    Carroll, AR
    Quinn, RJ
    Griffith University Author(s)
    Quinn, Ronald J.
    Davis, Rohan A.
    Carroll, Anthony R.
    Year published
    2002
    Metadata
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    Abstract
    Chemical investigation of a Great Barrier Reef ascidian, Aplidium tabascum, has resulted in the isolation of three new cis-decahydroquinoline alkaloids, lepadins F-H (4-6). The three new compounds differ from the previously isolated lepadins A-C (1-3) in that they contain a fully saturated 5-hydroxyoctyl side chain attached at C-5, an unsaturated eight-carbon ester moiety attached to C-3, and opposite stereochemistry at C-5 and C-3. Lepadins G (5) and H (6) are epimers at C-2. NMR and molecular modeling studies indicated that the three new compounds adopt a chair-chair conformation in which the nitrogen equatorially substitutes ...
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    Chemical investigation of a Great Barrier Reef ascidian, Aplidium tabascum, has resulted in the isolation of three new cis-decahydroquinoline alkaloids, lepadins F-H (4-6). The three new compounds differ from the previously isolated lepadins A-C (1-3) in that they contain a fully saturated 5-hydroxyoctyl side chain attached at C-5, an unsaturated eight-carbon ester moiety attached to C-3, and opposite stereochemistry at C-5 and C-3. Lepadins G (5) and H (6) are epimers at C-2. NMR and molecular modeling studies indicated that the three new compounds adopt a chair-chair conformation in which the nitrogen equatorially substitutes the cyclohexyl ring. This contrasts with lepadins A-C (1-3), which adopt a chair-chair conformation in which the nitrogen axially substitutes the cyclohexyl ring.
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    Journal Title
    Journal of Natural Products
    Volume
    65
    Publisher URI
    http://pubs.acs.org/loi/jnprdf
    DOI
    https://doi.org/10.1021/np010407x
    Copyright Statement
    © 2002 American Chemical Society. Self-archiving of the author-manuscript version is not yet supported by this publisher. The contents of this journal can be freely accessed online via the ACS web page. Use hypertext link above to access the ACS website.
    Subject
    Chemical sciences
    Biological sciences
    Biomedical and clinical sciences
    Traditional, complementary and integrative medicine
    Publication URI
    http://hdl.handle.net/10072/7006
    Collection
    • Journal articles

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