Quantitation of estragole by stable isotope dilution assays

Zeller, Annette; Rychlik, Michael

doi:10.1016/j.lwt.2008.10.011

Cited by 6 publications

(6 citation statements)

References 9 publications

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“…Estragole and trans-anethole were purchased from Aldrich (Steinheim, Germany). [1′′,1′′,1′′-2 H 3 ]-Estragole (13), pallylphenol (13), and p-methoxycinnamyl alcohol (14) were synthesized as described in the literature. OHE and [1′′,1′′,1′′-2 H 3 ]-OHE were synthesized by the following procedures.…”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of [1′′,1′′,1′′-2 H 3 ]-OHE (3b). p-Hydroxybenzaldehyde (1) was methylized using [ 2 H 3 ]-methyl iodide (13). The subsequent Grignard reaction with vinyl magnesium chloride as described before resulted in the formation of labeled OHE.…”

Section: Methodsmentioning

confidence: 99%

“…Quantification of Estragole in Fennel Tea Made from Fennel Fruits. Quantification of estragole in fennel tea was performed as described recently (13). Fennel tea was prepared by extracting 2.5 g of broken fennel fruits (Foeniculum Vulgare Mill.…”

Section: Methodsmentioning

confidence: 99%

“…The organic phase was dried over anhydrous sodium sulfate, concentrated to 2 mL, and analyzed by high-resolution gas chromatography and mass spectrometry (HRGC-MS) in CI mode. Estragole was quantified by relative area counts of analyte and internal standard (IS) using the response factor detailed previously (13).…”

Section: Methodsmentioning

confidence: 99%

“…The distillates were dried over anhydrous sodium sulfate, and the solvent was removed completely. The residue was dissolved in 300 µL of methanol and analyzed by GC-GC-MS. Quantification was performed by relative area counts of analyte and IS using the response factors detailed previously (13).…”

Section: Methodsmentioning

confidence: 99%

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Study of the Metabolism of Estragole in Humans Consuming Fennel Tea

Zeller

Horst

Rychlik

2009

Chem. Res. Toxicol.

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The metabolism of the potent carcinogen estragole was investigated in humans after consumption of fennel tea by analyses of its metabolites in blood plasma and urine. Stable isotope dilution assays based on LC-MS/MS detection revealed that 1'-hydroxylation of estragole happened very fast as the concentration of conjugated 1'-hydroxyestragole in urine peaked after 1.5 h, whereas it was no longer detectable after 10 h. Besides the formation of less than 0.41% conjugated 1'-hydroxyestragole of the estragole dose administered, the further metabolite p-allylphenol was generated from estragole in a higher percentage (17%). Both metabolites were also detected in blood plasma in less than 0.75-2.5 h after consumption of fennel tea. In contrast to this, no estragole was present in these samples above its detection limit. From the results, it can be concluded that an excess of the major fennel odorant trans-anethole principally does not interfere with estragole metabolism, whereas influences on the quantitative composition of metabolites cannot be excluded. The presence of a sulfuric acid conjugate of estragole could not be confirmed, possibly due to its high reactivity and lability.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Study of the Metabolism of Estragole in Humans Consuming Fennel Tea

Zeller

Horst

Rychlik

2009

Chem. Res. Toxicol.

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Quantification of 1,8‐cineole and of its metabolites in humans using stable isotope dilution assays

Horst

Rychlik

2010

Molecular Nutrition Food Res

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The metabolism of 1,8-cineole after ingestion of sage tea was studied. After application of the tea, the metabolites 2-hydroxy-1,8-cineole, 3-hydroxy-1,8-cineole, 9-hydroxy-1,8-cineole and, for the first time in humans, 7-hydroxy-1,8-cineole were identified in plasma and urine of one volunteer. For quantitation of these metabolites and the parent compound, stable isotope dilution assays were developed after synthesis of [(2)H(3)]-1,8-cineole, [9/10-(2)H(3)]-2-hydroxy-1,8-cineole and [(13)C,(2)H(2)]-9-hydroxy-1,8-cineole as internal standards. Using these standards, we quantified 1,8-cineole by solid phase microextraction GC-MS and the hydroxyl-1,8-cineoles by LC-MS/MS after deconjugation in blood and urine of the volunteer. After consumption of 1.02 mg 1,8-cineole (19 μg/kg bw), the hydroxycineoles along with their parent compound were detectable in the blood plasma of the volunteer under study after liberation from their glucuronides with 2-hydroxycineole being the predominant metabolite at a maximum plasma concentration of 86 nmol/L followed by the 9-hydroxy isomer at a maximum plasma concentration of 33 nmol/L. The parent compound 1,8-cineole showed a low maximum plasma concentration of 19 nmol/L. In urine, 2-hydroxycineole also showed highest contents followed by its 9-isomer. Summing up the urinary excretion over 10 h, 2-hydroxycineole, the 9-isomer, the 3-isomer and the 7-isomer accounted for 20.9, 17.2, 10.6 and 3.8% of the cineole dose, respectively.

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Metabolism of Odorants in Humans

Rychlik

2017

Springer Handbook of Odor

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Quantitation of estragole by stable isotope dilution assays

Cited by 6 publications

References 9 publications

Study of the Metabolism of Estragole in Humans Consuming Fennel Tea

Study of the Metabolism of Estragole in Humans Consuming Fennel Tea

Quantification of 1,8‐cineole and of its metabolites in humans using stable isotope dilution assays

Metabolism of Odorants in Humans

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