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

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Keywords

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

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