The analysis of pyrrolizidine alkaloids in Jacobaea vulgaris; a comparison of extraction and detection methods

Joosten, Lotte; Mulder, Patrick P.J.; Vrieling, Klaas; Veen, Johannes A. van; Klinkhamer, Peter G. L.

doi:10.1002/pca.1183

Cited by 33 publications

(18 citation statements)

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“…We found consistently large amounts of tertiary amines in Jacobaea vulgaris plants (Joosten et al, 2009(Joosten et al, , 2010. However, the general tendency in literature is that tertiary amines are present only in very small amounts and maybe are due to artifacts during extraction or detection Hartmann, 1999;Hartmann and Ober, 2000).…”

Section: Introductionmentioning

confidence: 78%

“…Recently liquid chromatography-tandem mass spectrometry (LC-MS/MS) has been introduced for measuring PAs in plant material. Unlike GC-related methods, LC-MS/MS and NMR can detect both tertiary amines and N-oxides without an additional reducing step (Crews et al, 2010;Joosten et al, 2010). However, NMR needs relatively high concentrations of PAs for detection.…”

Section: Introductionmentioning

confidence: 96%

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

et al. 2011

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Section: Introductionmentioning

confidence: 78%

Section: Introductionmentioning

confidence: 96%

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

et al. 2011

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“…Jacobaea (Pelser et al. , 2005), although the recent development of more sensitive analytical methods has allowed the detection of a greater number of structural PA variants in the same species (Joosten et al. , 2009, 2010, 2011).…”

Section: Introductionmentioning

confidence: 99%

Pyrrolizidine alkaloid variation in shoots and roots of segregating hybrids between Jacobaea vulgaris and Jacobaea aquatica

et al. 2011

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Summary• Hybridization can lead to novel qualitative or quantitative variation of secondary metabolite (SM) expression that can have ecological and evolutionary consequences.• We measured pyrrolizidine alkaloid (PA) expression in the shoots and roots of a family including one Jacobaea vulgaris genotype and one Jacobaea aquatica genotype (parental genotypes), two F 1 hybrid genotypes, and 102 F 2 hybrid genotypes using liquid chromatography-tandem mass spectrometry (LC-MS ⁄ MS).• We detected 37 PAs in the roots and shoots of J. vulgaris, J. aquatica and the hybrids. PA concentrations and compositions differed between genotypes, and between roots and shoots. Three otosenine-like PAs that only occurred in the shoots of parental genotypes were present in the roots of F 2 hybrids; PA compositions were sometimes novel in F 2 hybrids compared with parental genotypes, and in some cases transgressive PA expression occurred. We also found that PAs from within structural groups covaried both in the roots and in the shoots, and that PA expression was correlated between shoots and roots.• Considerable and novel variation present among F 2 hybrids indicates that hybridization has a potential role in the evolution of PA diversity in the genus Jacobaea, and this hybrid system is useful for studying the genetic control of PA expression.

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“…The fact that no reduction step is needed, may lead to simplified and less elaborate protocols. A recent method for the simultaneous detection of PAs and PANOs in Jacobaea vulgaris with subsequent liquid chromatography-tandem mass spectrometry (LC-MS/MS) (Joosten et al, 2010) or ultra high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) detection uses a single step extraction of lyophilized ground plant material with 2 % aqueous formic acid solution for 30 min, microfiltration and dilution prior to analysis (Joosten et al, 2011).…”

Section: Extractionmentioning

confidence: 99%

Scientific Opinion on Pyrrolizidine alkaloids in food and feed

2011

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The European Food Safety Authority (EFSA) was asked by the European Commission to deliver a scientific opinion on pyrrolizidine alkaloids (PA) in food and feed. PAs are toxins exclusively biosynthesised by plants. To date, approximately 600 different PAs are known. Results for 13,280 bulk honey and 1324 retail honey samples were provided to EFSA by one Member State and 351 feed samples were provided by a second Member State. The EFSA Panel on Contaminants in the Food Chain (CONTAM Panel) performed estimates of both acute and chronic exposure to PAs through honey for three different age groups. Although there might be other sources of PA exposure, due to lack of data the CONTAM Panel was not able to quantify dietary exposure from food other than honey. A number of PAs were identified as being of particular importance for food and feed. Based on the present knowledge of metabolism, activation, DNA adduct-formation, genotoxicity and carcinogenicity, the CONTAM Panel concluded that 1,2-unsaturated PAs may act as genotoxic carcinogens in humans. Therefore, the CONTAM Panel decided to apply the Margin of Exposure (MOE) approach. A benchmark dose lower confidence limit for a 10 % excess cancer risk (BMDL 10 ) of 70 µg/kg b.w. per day for induction of liver haemangiosarcomas by lasiocarpine in male rats was calculated as the reference point for comparison with the estimated dietary exposure. The CONTAM Panel concluded that there is a possible health concern for those toddlers and children who are high consumers of honey. There is generally a low risk of PA poisoning in livestock and companion animals in the EU as most PA poisonings reported recently are due to accidental exposure. © European Pyrrolizidine alkaloids in food and feedEFSA Journal 2011;9(11):2406 2 SUMMARYFollowing a request from the European Commission, the Panel on Contaminants in the Food Chain (CONTAM Panel) was asked to deliver a scientific opinion on the risks to human and animal health related to the presence of pyrrolizidine alkaloids (PA) in food and feed. PAs are toxins exclusively biosynthesised by plants. They are typical plant secondary metabolites against herbivores. It has been estimated that approximately 6000 plant species world wide, representing 3 % of all flowering plants, may contain pyrrolizidine alkaloids. PAs are mainly found in the distantly related angiosperm families of the Boraginaceae (all genera), Asteraceae (tribes Senecioneae and Eupatorieae) and Fabaceae (genus Crotalaria). The PA-content of plant material depends on a large number of factors (species, plant organ, harvest, storage, extraction procedures). Reported contents vary from trace amounts up to 19 % based on dry weight. The name pyrrolizidine is the chemical description of two-fused 5-membered rings with a nitrogen atom at the bridgehead. This motif is the central structure of a variety of PAs. PAs generally consist of an amino alcohol which is referred to as necine or necine base and an acid part which is called a necic acid. Most of the known PAs are este...

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The analysis of pyrrolizidine alkaloids in Jacobaea vulgaris; a comparison of extraction and detection methods

Abstract: In terms of sensitivity and discrimination, formic acid extraction in combination with LC-MS/MS detection is the method of choice for analysing PAs (both free and N-oxides forms) in plant material.

Cited by 33 publications

References 30 publications

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

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

Pyrrolizidine alkaloid variation in shoots and roots of segregating hybrids between Jacobaea vulgaris and Jacobaea aquatica

Scientific Opinion on Pyrrolizidine alkaloids in food and feed

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