The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in jacobaea vulgaris

L. Joosten, D. Cheng, P.P.J. Mulder, K. Vrieling, J.A. van Veen, P.G.L. Klinkhamer

    Research output: Contribution to journalArticleAcademicpeer-review

    21 Citations (Scopus)

    Abstract

    Secondary metabolites such as pyrrolizidine alkaloids (PAs) play a crucial part in plant defense. PAs can occur in plants in two forms: tertiary amine (free base) and N-oxide. PA extraction and detection are of great importance for the understanding of the role of PAs as plant defense compounds, as the tertiary PA form is known for its stronger influence on several generalist insects, whereas the N-oxide form is claimed to be less deterrent. We measured PA N-oxides and their reduced tertiary amines by liquid chromatography–tandem mass spectrometry (LC-MS/MS). We show that the occurrence of tertiary PAs is not an artifact of the extraction and detection method. We found up to 50% of tertiary PAs in shoots of Jacobine – chemotype plants of Jacobaea vulgaris. Jacobine and its derivatives (jacoline, jaconine, jacozine and dehydrojaconine) may occur for more than 20% in reduced form in the shoots and more than 10% in the roots. For 22 PAs detected in F2 hybrids (J. vulgaris × Jacobaea aquatica), we calculate the tertiary amine percentage (TA% = the tertiary amine concentration/(tertiary amine concentration + the corresponding N-oxide concentration) × 100). We found that the TA% for various PAs was genotype-dependent. Furthermore, TA% for the different PAs were correlated and the highest correlations occurred between PAs which share high structural similarity. --------------------------------------------------------------------------------
    Original languageEnglish
    Pages (from-to)214-222
    Number of pages9
    JournalPhytochemistry
    Volume72
    Issue number2-3
    DOIs
    Publication statusPublished - 2011

    Fingerprint

    tertiary amines
    Senecio jacobaea
    Pyrrolizidine Alkaloids
    pyrrolizidine alkaloids
    Amines
    Genotype
    genotype
    Oxides
    oxides
    shoots
    chemotypes
    Metabolites
    Artifacts
    secondary metabolites
    plant anatomy

    Keywords

    • senecio-jacobaea
    • n-oxides
    • root cultures
    • plants
    • insects
    • hybridization
    • biosynthesis
    • metabolism
    • herbivores
    • transport

    Cite this

    Joosten, L. ; Cheng, D. ; Mulder, P.P.J. ; Vrieling, K. ; van Veen, J.A. ; Klinkhamer, P.G.L. / The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in jacobaea vulgaris. In: Phytochemistry. 2011 ; Vol. 72, No. 2-3. pp. 214-222.
    @article{e89637f70c65488c85121883537f572e,
    title = "The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in jacobaea vulgaris",
    abstract = "Secondary metabolites such as pyrrolizidine alkaloids (PAs) play a crucial part in plant defense. PAs can occur in plants in two forms: tertiary amine (free base) and N-oxide. PA extraction and detection are of great importance for the understanding of the role of PAs as plant defense compounds, as the tertiary PA form is known for its stronger influence on several generalist insects, whereas the N-oxide form is claimed to be less deterrent. We measured PA N-oxides and their reduced tertiary amines by liquid chromatography–tandem mass spectrometry (LC-MS/MS). We show that the occurrence of tertiary PAs is not an artifact of the extraction and detection method. We found up to 50{\%} of tertiary PAs in shoots of Jacobine – chemotype plants of Jacobaea vulgaris. Jacobine and its derivatives (jacoline, jaconine, jacozine and dehydrojaconine) may occur for more than 20{\%} in reduced form in the shoots and more than 10{\%} in the roots. For 22 PAs detected in F2 hybrids (J. vulgaris × Jacobaea aquatica), we calculate the tertiary amine percentage (TA{\%} = the tertiary amine concentration/(tertiary amine concentration + the corresponding N-oxide concentration) × 100). We found that the TA{\%} for various PAs was genotype-dependent. Furthermore, TA{\%} for the different PAs were correlated and the highest correlations occurred between PAs which share high structural similarity. --------------------------------------------------------------------------------",
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    language = "English",
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    pages = "214--222",
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    The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in jacobaea vulgaris. / Joosten, L.; Cheng, D.; Mulder, P.P.J.; Vrieling, K.; van Veen, J.A.; Klinkhamer, P.G.L.

    In: Phytochemistry, Vol. 72, No. 2-3, 2011, p. 214-222.

    Research output: Contribution to journalArticleAcademicpeer-review

    TY - JOUR

    T1 - The genotype dependent presence of pyrrolizidine alkaloids as tertiary amine in jacobaea vulgaris

    AU - Joosten, L.

    AU - Cheng, D.

    AU - Mulder, P.P.J.

    AU - Vrieling, K.

    AU - van Veen, J.A.

    AU - Klinkhamer, P.G.L.

    PY - 2011

    Y1 - 2011

    N2 - Secondary metabolites such as pyrrolizidine alkaloids (PAs) play a crucial part in plant defense. PAs can occur in plants in two forms: tertiary amine (free base) and N-oxide. PA extraction and detection are of great importance for the understanding of the role of PAs as plant defense compounds, as the tertiary PA form is known for its stronger influence on several generalist insects, whereas the N-oxide form is claimed to be less deterrent. We measured PA N-oxides and their reduced tertiary amines by liquid chromatography–tandem mass spectrometry (LC-MS/MS). We show that the occurrence of tertiary PAs is not an artifact of the extraction and detection method. We found up to 50% of tertiary PAs in shoots of Jacobine – chemotype plants of Jacobaea vulgaris. Jacobine and its derivatives (jacoline, jaconine, jacozine and dehydrojaconine) may occur for more than 20% in reduced form in the shoots and more than 10% in the roots. For 22 PAs detected in F2 hybrids (J. vulgaris × Jacobaea aquatica), we calculate the tertiary amine percentage (TA% = the tertiary amine concentration/(tertiary amine concentration + the corresponding N-oxide concentration) × 100). We found that the TA% for various PAs was genotype-dependent. Furthermore, TA% for the different PAs were correlated and the highest correlations occurred between PAs which share high structural similarity. --------------------------------------------------------------------------------

    AB - Secondary metabolites such as pyrrolizidine alkaloids (PAs) play a crucial part in plant defense. PAs can occur in plants in two forms: tertiary amine (free base) and N-oxide. PA extraction and detection are of great importance for the understanding of the role of PAs as plant defense compounds, as the tertiary PA form is known for its stronger influence on several generalist insects, whereas the N-oxide form is claimed to be less deterrent. We measured PA N-oxides and their reduced tertiary amines by liquid chromatography–tandem mass spectrometry (LC-MS/MS). We show that the occurrence of tertiary PAs is not an artifact of the extraction and detection method. We found up to 50% of tertiary PAs in shoots of Jacobine – chemotype plants of Jacobaea vulgaris. Jacobine and its derivatives (jacoline, jaconine, jacozine and dehydrojaconine) may occur for more than 20% in reduced form in the shoots and more than 10% in the roots. For 22 PAs detected in F2 hybrids (J. vulgaris × Jacobaea aquatica), we calculate the tertiary amine percentage (TA% = the tertiary amine concentration/(tertiary amine concentration + the corresponding N-oxide concentration) × 100). We found that the TA% for various PAs was genotype-dependent. Furthermore, TA% for the different PAs were correlated and the highest correlations occurred between PAs which share high structural similarity. --------------------------------------------------------------------------------

    KW - senecio-jacobaea

    KW - n-oxides

    KW - root cultures

    KW - plants

    KW - insects

    KW - hybridization

    KW - biosynthesis

    KW - metabolism

    KW - herbivores

    KW - transport

    U2 - 10.1016/j.phytochem.2010.11.013

    DO - 10.1016/j.phytochem.2010.11.013

    M3 - Article

    VL - 72

    SP - 214

    EP - 222

    JO - Phytochemistry

    JF - Phytochemistry

    SN - 0031-9422

    IS - 2-3

    ER -