Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1'-hydroxyestragole.

@article{Anthony1987MetabolismOE,
  title={Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1'-hydroxyestragole.},
  author={A Anthony and John Caldwell and Andrew J. Hutt and R. Smith},
  journal={Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association},
  year={1987},
  volume={25 11},
  pages={
          799-806
        }
}
  • A. Anthony, J. Caldwell, R. Smith
  • Published 1 November 1987
  • Biology, Medicine
  • Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association
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In vivo validation of DNA adduct formation by estragole in rats predicted by physiologically based biodynamic modelling.
TLDR
The results obtained provide the first data set available on estragole-DNA adduct formation in rats and confirm their occurrence in metabolically active tissues, i.e. liver, lung and kidney, while the significantly higher levels found in liver are in accordance with the liver as the target organ for carcinogenicity.
Matrix modulation of the bioactivation of estragole by constituents of different alkenylbenzene-containing herbs and spices and physiologically based biokinetic modeling of possible in vivo effects.
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The PBBK-model-based predictions indicate that the reduction of estragole bioactivation in rat and human by co-administration of the flavonoids is dependent on whether the intracellular liver concentrations of the Flavonoids can reach their Ki values.
Use of Physiologically Based Biokinetic (PBBK) Modeling to Study Estragole Bioactivation and Detoxification in Humans as Compared with Male Rats
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  • Biology, Chemistry
    Toxicological sciences : an official journal of the Society of Toxicology
  • 2009
TLDR
It is concluded that in spite of significant differences in the relative extent of different metabolic pathways between human and male rat there is a minor influence of species differences on the ultimate overall bioactivation of estragole to 1′-sulfooxyestragole.
Matrix modulation of the toxicity of alkenylbenzenes, studied by an integrated approach using in vitro, in vivo, and physiologically based biokinetic models
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The results predict that co-administration of estragole at a level inducing hepatic tumours in vivo (50 mg/kg bw) with nevadensin at a molar ratio of 0.06 results in almost 100% inhibition of the ultimate carcinogen 1′-sulfooxyestragole when assuming 100% uptake of nevdensin.
Evaluation of human interindividual variation in bioactivation of estragole using physiologically based biokinetic modeling.
TLDR
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  • 1990
Study on inter-ethnic human differences in bioactivation and detoxification of estragole using physiologically based kinetic modeling
TLDR
The study provides a proof of principle for how PBK modeling can identify differences in ethnic sensitivity and provide a more refined risk assessment for a specific ethnic group for a compound of concern.
...
...

References

SHOWING 1-10 OF 13 REFERENCES
Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1'-hydroxyestragole in the mouse and mutagenicity of 1'-acetoxyestragole in bacteria.
TLDR
Estragole induced hepatocellular carcinomas by 15 months in 23 and 39% of the mice that received total doses of 4.4 and 5.2 mumoles, respectively, and lived to an age of 12 months or more, and 1'-Acetoxyallybenzene had little or no activity in either of these tests.
Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole.
TLDR
Twenty-three naturally occurring and synthetic alkenylbenzene derivatives structurally related to the hepatocarcinogen safrole were assayed for their hepatocARCinogenicity in mice to identify benign skin tumors that could be promoted with croton oil.
The metabolism of p-propylanisole in the rat and mouse and its variation with dose.
The metabolic disposition of [methoxy-14C]-labelled trans-anethole, estragole and p-propylanisole in human volunteers.
1. The metabolic fates of the naturally occurring food flavours trans-anethole and estragole, and their synthetic congener p-propylanisole, have been investigated in human volunteers using the
Structures of the DNA adducts formed in mouse liver after administration of the proximate hepatocarcinogen 1'-hydroxyestragole.
TLDR
All four adducts in the mouse liver can be accounted for by the reaction of a metabolically derived ester of 1′-hydroxyestragole with purine bases in DNA by SN1, SN2, or SN2′ mechanisms.
The Concept of Reactive Electrophilic Metabolites in Chemical Carcinogenesis: Recent Results with Aromatic Amines, Safrole, and Aflatoxin B1
TLDR
Although most drugs and their metabolites probably interact only noncovalently and thus reversibly with cellular molecules in their pharmacological actions, closer inspection of the metabolism of various drugs will doubtless reveal various degrees of covalent interactions in vivo.
Metabolism of [14C]methamphetamine in man, the guinea pig and the rat
TLDR
The main reaction in the rat was aromatic hydroxylation, in the guinea pig demethylation and deamination, whereas in man much of the drug, possibly one-half, was excreted unchanged, and Marked species differences in the metabolism of methamphetamine were observed.
Biotransformation of allylbenzene analogues in vivo and in vitro through the epoxide-diol pathway.
1. The epoxidation of allylbenzene, safrole, estragole, eugenol and eugenol methyl ether was investigated in rats pretreated with these compounds and also in vitro using hepatic microsomal
Implication of nonlinear kinetics on risk estimation in carcinogenesis.
TLDR
Of particular importance is the possibility that the kinetic processes involved in the formation of carcinogen metabolite--DNA adducts may show a nonlinear "hockey-stick" like behavior which results from saturation of detoxification or DNA repair processes.
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