The polyketide folding mode in the biogenesis of isoshinanolone and plumbagin from Ancistrocladus heyneanus (Ancistrocladaceae)

G. Bringmann (Corresponding Author), M. Wohlfarth, Heiko Rischer, M. Rückert, J. Schlauer

    Research output: Contribution to journalArticleScientificpeer-review

    36 Citations (Scopus)

    Abstract

    The biosynthetic orgins of the tetralone isoshinanolone and the related naphthoquinone plumbagin were investigated by feeding [13C2]-acetate to suspended callus cultures of Ancistrocladus heyneanus. The orientation of the acetate subunits was elucidated by a similar experiment using [2-13C]-acetate. The polyketide folding mode found for isoshinanolone and plumbagin constitutes a further hint at the acetogenic nature of the naphthylisoquinoline alkaloids, which are typical of A. heyneanus and other species of Ancistrocladaceae and Dioncophyllaceae.

    The acetogenic origin and the polyketide folding mode of the naphthoquinone plumbagin (5) and the tetralone isoshinanolone (6) in Ancistrocladus heyneanus were established by feeding of differently 13C-labelled acetate and subsequent 13C NMR analysis.
    Original languageEnglish
    Pages (from-to)8445-8448
    JournalTetrahedron Letters
    Volume39
    Issue number46
    DOIs
    Publication statusPublished - 1998
    MoE publication typeA1 Journal article-refereed

    Fingerprint

    Dive into the research topics of 'The polyketide folding mode in the biogenesis of isoshinanolone and plumbagin from Ancistrocladus heyneanus (Ancistrocladaceae)'. Together they form a unique fingerprint.

    Cite this