Anatalline and other methyl jasmonate-inducible nicotine alkaloids from Nicotiana tabacum cv. BY-2 cell cultures

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    Abstract

    Anatalline [2,4-di(3-pyridyl)piperidine] accumulation was shown to be induced by methyl jasmonate in Nicotiana tabacum cv. BY-2 cell cultures. Beside anatabine, anatalline represented the most abundant alkaloid, moreover, it was always present in two isomeric forms occurring always in similar concentrations. Both isomers could be completely separated by GC-MS. For structural analysis, the isolation of both isomers was performed using a semi-preparative HPLC system. The structures of anatalline [cis-2,4-di(3-pyridyl)piperidine] and its stereoisomer trans-2,4-di(3-pyridyl)piperidine were confirmed by MS and 1D and 2D NMR spectral data. The biosynthetic origin of anatalline was studied by feeding alkaloid precursors to BY-2 cell cultures.
    Original languageEnglish
    Pages (from-to)936 - 941
    Number of pages6
    JournalPlanta Medica
    Volume70
    Issue number10
    DOIs
    Publication statusPublished - 2004
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Nicotiana tabacum BY-2
    • Solanaceae
    • alkaloids
    • anatalline
    • anatabine
    • cell cultures

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