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

Suvi T. Häkkinen; Heiko Rischer; Into Laakso; Hannu Maaheimo; Tuulikki Seppänen-Laakso; Kirsi-Marja Oksman-Caldentey

doi:10.1055/s-2004-832620

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

Suvi T. Häkkinen, Heiko Rischer, Into Laakso, Hannu Maaheimo, Tuulikki Seppänen-Laakso, Kirsi-Marja Oksman-Caldentey

University of Helsinki

Research output: Contribution to journal › Article › Scientific › peer-review

24 Citations (Scopus)

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 language	English
Pages (from-to)	936 - 941
Number of pages	6
Journal	Planta Medica
Volume	70
Issue number	10
DOIs	https://doi.org/10.1055/s-2004-832620
Publication status	Published - 2004
MoE publication type	A1 Journal article-refereed

Keywords

Nicotiana tabacum BY-2
Solanaceae
alkaloids
anatalline
anatabine
cell cultures

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10.1055/s-2004-832620

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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",

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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

SN - 0032-0943

VL - 70

SP - 936

EP - 941

JO - Planta Medica

JF - Planta Medica

IS - 10

ER -

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

Abstract

Keywords

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