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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Nicotine
Cell culture
Alkaloids
Tobacco
Cell Culture Techniques
Isomers
Stereoisomerism
methyl jasmonate
anatalline
Structural analysis
High Pressure Liquid Chromatography
Nuclear magnetic resonance

Keywords

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

Cite this

@article{588363d9de854d3bb05b0f162b0ee3dc,
title = "Anatalline and other methyl jasmonate-inducible nicotine alkaloids from Nicotiana tabacum cv. BY-2 cell cultures",
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.",
keywords = "Nicotiana tabacum BY-2, Solanaceae, alkaloids, anatalline, anatabine, cell cultures",
author = "H{\"a}kkinen, {Suvi T.} and Heiko Rischer and Into Laakso and Hannu Maaheimo and Tuulikki Sepp{\"a}nen-Laakso and Kirsi-Marja Oksman-Caldentey",
year = "2004",
doi = "10.1055/s-2004-832620",
language = "English",
volume = "70",
pages = "936 -- 941",
journal = "Planta Medica",
issn = "0032-0943",
publisher = "Georg Thieme Verlag",
number = "10",

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TY - JOUR

T1 - Anatalline and other methyl jasmonate-inducible nicotine alkaloids from Nicotiana tabacum cv. BY-2 cell cultures

AU - Häkkinen, Suvi T.

AU - Rischer, Heiko

AU - Laakso, Into

AU - Maaheimo, Hannu

AU - Seppänen-Laakso, Tuulikki

AU - Oksman-Caldentey, Kirsi-Marja

PY - 2004

Y1 - 2004

N2 - 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.

AB - 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.

KW - Nicotiana tabacum BY-2

KW - Solanaceae

KW - alkaloids

KW - anatalline

KW - anatabine

KW - cell cultures

U2 - 10.1055/s-2004-832620

DO - 10.1055/s-2004-832620

M3 - Article

C2 - 15490322

VL - 70

SP - 936

EP - 941

JO - Planta Medica

JF - Planta Medica

SN - 0032-0943

IS - 10

ER -