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A sensitive analytical method for pyrrolizidine alkaloids. The mass spectra of retronecine derivatives.

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The pyrrolizidine alkaloids in Senecio jacobaea can be hydrolyzed to the common base, retronecine, and derivatized to form the bistrifluoroacetate, bisheptafluorobutyrate, diacetate and bistrimethylsilyl ether. The analysis of the fluorinated compounds by electron capture provides sensitivity for

Synthesis of [3,5-14C]trachelanthamidine and [5-3H]isoretronecanol and their incorporation into the retronecine moiety of riddelliine in Senecio riddellii.

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(+/-)-[3,5-14C]Trachelanthamidine and (+/-)-[5-3H]isoretronecanol, which are diastereomers, were prepared from potassium [14C]cyanide and [5-3H]proline, respectively. These compounds and [1,4-14C]putrescine were administered to Senecio riddellii plants resulting in the formation of labeled

Quantitative analysis of total retronecine esters-type pyrrolizidine alkaloids in plant by high performance liquid chromatography.

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Pyrrolizidine alkaloids (PAs) are alkaloids which typically contain a necine (7-hydroxy-1-hydroxymethyl-6,7-dihydro-5H-pyrrolizidine) base unit, and they can be found in one third of the higher plants around the world. They are hepatotoxic, mutagenic and carcinogenic and pose a threat to human

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

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Changes in plant chemical defenses after invasion could have consequences on the invaded ecosystems by modifying the interactions between plants and herbivores and facilitating invasion success. However, no comprehensive biogeographical studies have yet determined the phenotypic levels of plant

Microsomal metabolism of pyrrolizidine alkaloids from Senecio jacobaea. Isolation and quantification of 6,7-dihydro-7-hydroxy-1-hydroxymethyl-5H-pyrrolizine and N-oxides by high performance liquid chromatography.

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The metabolism in vitro of four pyrrolizidine alkaloids from the poisonous plant Senecio jacobaea was studied. The pyrrolizidine alkaloids jacobine, jacoline, senecionine, and seneciphylline, all macrocyclic diesters of retronecine, were incubated with rat liver microsomes. Analysis of incubation

Pyrrolizidine alkaloids in honey: comparison of analytical methods.

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Pyrrolizidine alkaloids (PAs) are a structurally diverse group of toxicologically relevant secondary plant metabolites. Currently, two analytical methods are used to determine PA content in honey. To achieve reasonably high sensitivity and selectivity, mass spectrometry detection is demanded. One

Identification of metabolites of adonifoline, a hepatotoxic pyrrolizidine alkaloid, by liquid chromatography/tandem and high-resolution mass spectrometry.

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Hepatotoxic pyrrolizidine alkaloid (HPA)-containing plants have always been a threat to human and livestock health worldwide. Adonifoline, a main HPA in Senecio scandens Buch.-Ham. ex D. Don (Qianli guang), was used officially as an infusion in cases of oral and pharyngeal infections in China. In

Pyrrolizidine alkaloids of three species of senecio in British Columbia.

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A new alkaloid, 9- O-acetyl-7- O-angelyl-retronecine, was isolated from Senecio triangularis together with 7-O-angelyl-, 9-O-angelyl-, and 7-O-angelyl-9-O-sarracinylretronecine; S. pseudaureus and S. streptanthifolios yielded only retrorsine and senecionine.

Hydrolysis rates of pyrrolizidine alkaloids derived from Senecio jacobaea.

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Many of the commonly studied pyrrolizidine alkaloids (PAs) are built upon the subgroup retronecine (RET), which is released from the parent molecule by either base catalyzed or enzymatic hydrolysis of the ester linkages. The rate of appearance of RET in a hydrolytic study would thus reflect the rate

Quantitative analysis by HPLC-MS2 of the pyrrolizidine alkaloid adonifoline in Senecio scandens.

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A quantitative method using HPLC-MS(2) has been developed for the determination of adonifoline, one of the retronecine-type hepatotoxic pyrrolizidine alkaloids in Senecio scandens Buch.-Ham. ex D. Don., a traditional Chinese herb. Using an orthogonal design test, a simple and rapid sample extraction

Pyrrolizidine alkaloids in pollen and pollen products.

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Recently, 1,2-dehydropyrrolizidine alkaloid (PA) ester alkaloids, found predominantly as their N-oxides (PANOs, pyrrolizidine N-oxides), have been reported in both honey and in pollen obtained directly from PA plants and pollen loads collected by bees, raising the possibility of health risks for

Transfer of [3H]pyrrolizidine alkaloids from Senecio vulgaris L. and metabolites into rat milk and tissues.

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[3H]Retronecine and [3H]necic acid-labelled senecionine and seneciphylline were prepared biosynthetically with seedlings of Senecio vulgaris L. using [2,3-3H]putrescine and [4,5-3H]isoleucine, respectively, as precursors. Lactating rats dosed with these differently labelled pyrrolizidine alkaloids

Macrocyclic pyrrolizidine alkaloids from Senecio anonymus. Separation of a complex alkaloid extract using droplet counter-current chromatography.

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Ten 12-membered macrocyclic pyrrolizidine alkaloids, all of them esters of the necines, retronecine or otonecine, have been isolated from Senecio anonymus. The separation, carried out by droplet counter-current chromatography, afforded senecionine [1], integerrimine [2], retrorsine [3], senkirkine

Frequent gain and loss of pyrrolizidine alkaloids in the evolution of Senecio section Jacobaea (Asteraceae).

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Pyrrolizidine alkaloids (PAs) of the macrocyclic senecionine type are secondary metabolites characteristic for most species of the genus Senecio (Asteraceae). These PAs are deterrent and toxic to most vertebrates and insects and provide plants with a chemical defense against herbivores. We studied

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