Taichunamides: Prenylated Indole Alkaloids from Aspergillus taichungensis (IBT 19404)

Ippei Kagiyama, Hikaru Kato, Tatsuo Nehira, Jens Christian Frisvad, David H. Sherman, Robert M. Williams, Sachiko Tsukamoto

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    Abstract

    Seven new prenylated indole alkaloids, taichunamides A–G, were isolated from the fungus Aspergillus taichungensis (IBT 19404). Taichunamides A and B contained an azetidine and 4‐pyridone units, respectively, and are likely biosynthesized from notoamide S via (+)‐6‐epi‐stephacidin A. Taichunamides C and D contain endoperoxide and methylsulfonyl units, respectively. This fungus produced indole alkaloids containing an anti‐bicyclo[2.2.2]diazaoctane core, whereas A. protuberus and A. amoenus produced congeners with a syn‐bicyclo[2.2.2]diazaoctane core. Plausible biosynthetic pathways to access these cores within the three species likely arise from an intramolecular hetero Diels–Alder reaction.
    Original languageEnglish
    JournalAngewandte Chemie International Edition
    Volume55
    Issue number3
    Pages (from-to)1128-1132
    Number of pages5
    ISSN1433-7851
    DOIs
    Publication statusPublished - 2016

    Keywords

    • Alkaloids
    • Biosynthesis
    • Cycloaddition
    • Natural products
    • Structure elucidation

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