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

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

doi:10.1016/j.phytochem.2010.11.013

Cited by 26 publications

(27 citation statements)

References 38 publications

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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

EFS2

222

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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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Section: Extractionmentioning

confidence: 99%

Scientific Opinion on Pyrrolizidine alkaloids in food and feed

2011

EFS2

222

130

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“…PAs are largely stored in the plant foliage in the non toxic N-oxide form (Joosten et al, 2009; but see Joosten et al, 2011). However, after ingested by herbivores they are reduced into tertiary amines in the gut and metabolized by cytochrome P 450 s, originating reactive metabolites that interact with proteins and nucleic acids (Hartmann, 1999;Fu et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): Implications for toxicity

2014

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“…Pyrrolizidine alkaloids are ester alkaloids composed of a necine base (amino alcohol moiety) and an alkyl, or rarely aralkyl, necic acid (Hartmann, 1999). PAs can occur in two forms in vivo , the tertiary amine (free base) or the N- oxide form (Hartmann et al, 1989; Rizk, 1991; Wiedenfeld et al, 2008; Joosten et al, 2011). In Jacobaea species, all PAs except for senecivernine are derived from senecionine N -oxide, which is synthesized in the roots, transported to the shoots, and diversified into other PA structures (Hartmann and Toppel, 1987).…”

Section: Introductionmentioning

confidence: 99%

The Relationship between Structurally Different Pyrrolizidine Alkaloids and Western Flower Thrips Resistance in F2 Hybrids of Jacobaea vulgaris and Jacobaea aquatica

et al. 2011

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Segregating plant hybrids often have more ecological and molecular variability compared to parental species, and are therefore useful for studying relationships between different traits, and the adaptive significance of trait variation. Hybrid systems have been used to study the relationship between the expression of plant defense compounds and herbivore susceptibility. We conducted a western flower thrips (WFT) bioassay using a hybrid family and investigated the relationship between WFT resistance and pyrrolizidine alkaloid (PA) variation. The hybrid family consisted of two parental (Jacobaea vulgaris and Jacobaea aquatica) genotypes, two F 1 genotypes, and 94 F 2 hybrid lines. The J. aquatica genotype was more susceptible to thrips attack than the J. vulgaris genotype, the two F 1 hybrids were as susceptible as J. aquatica, and susceptibility to WFT differed among F 2 hybrid lines: 69 F 2 lines were equally susceptible compared to J. aquatica, 10 F 2 lines were more susceptible than J. aquatica and 15 F 2 lines were as resistant as J. vulgaris or were intermediate to the two parental genotypes. Among 37 individual PAs that were derived from four structural groups (senecionine-, jacobine-, erucifoline-and otosenine-like PAs), the Noxides of jacobine, jaconine, and jacoline were negatively correlated with feeding damage caused by WFT, and the tertiary amines of jacobine, jaconine, jacoline, and other PAs did not relate to feeding damage. Total PA concentration was negatively correlated with feeding damage. Among the four PA groups, only the total concentration of the jacobine-like PAs was negatively correlated with feeding damage. Multiple regression tests suggested that jacobine-like PAs play a greater role in WFT resistance than PAs from other structural groups. We found no evidence for synergistic effects of different PAs on WFT resistance. The relationship between PA variation and WFT feeding damage in the Jacobaea hybrids suggests a role for PAs in resistance to generalist insects.

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

Cited by 26 publications

References 38 publications

Scientific Opinion on Pyrrolizidine alkaloids in food and feed

Scientific Opinion on Pyrrolizidine alkaloids in food and feed

Diversity of pyrrolizidine alkaloids in native and invasive Senecio pterophorus (Asteraceae): Implications for toxicity

The Relationship between Structurally Different Pyrrolizidine Alkaloids and Western Flower Thrips Resistance in F2 Hybrids of Jacobaea vulgaris and Jacobaea aquatica

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