Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: its relevance to R-(+)-pulegone-mediated hepatotoxicity.

@article{Madyastha2002StereoselectiveHO,
  title={Stereoselective hydroxylation of 4-methyl-2-cyclohexenone in rats: its relevance to R-(+)-pulegone-mediated hepatotoxicity.},
  author={Kattigere M. Madyastha and Chellan Paul Raj},
  journal={Biochemical and biophysical research communications},
  year={2002},
  volume={297 2},
  pages={
          202-5
        }
}
  • K. M. Madyastha, C. P. Raj
  • Published 20 September 2002
  • Chemistry, Biology
  • Biochemical and biophysical research communications
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TLDR
In vitro studies carried out in vitro demonstrated that hydroxylation at the tertiary carbon atom or oxidation of the isopropylidene methyl groups in II can be specifically blocked through structural modifications as seen in compounds 2,2-dimethyl-5-(1-methylethylidane)-cyclopentanone (III) and 5-methyl-2-ethyl-1-propylidenes-cyclopent anone (IV).
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TLDR
Based on results, metabolic pathways for the biotransformation of R-(+)-pulegone in rat have been proposed and eight new metabolites have now been isolated from rat urine.
Evidence for the formation of a known toxin, p-cresol, from menthofuran.
Role of C-5 chiral center in R-(+)-pulegone-mediated hepatotoxicity: metabolic disposition and toxicity of 5, 5-dimethyl-2-(1-Methylethylidene)-cyclohexanone in rats.
TLDR
It is suggested that PB-induced cytochrome P-450-catalyzed reactive metabolites may be responsible for the toxic effects caused by 5, 5-dimethyl-2-(1-methylethylidene)-cyclohexanone, and pretreatment with 3-methylcholanthrene protected from it.
Metabolic disposition of a monoterpene ketone, piperitenone, in rats: evidence for the formation of a known toxin, p-cresol.
TLDR
A probable mechanism for the formation of p-cresol from piperitenone (I) via the intermediacy of metabolite III has been proposed.
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TLDR
Based on these studies, metabolic pathways for the biotransformation of S-(-)-pulegone in rat have been proposed and possible reasons for the observed difference in the toxicity mediated by these two enantiomers are discussed.
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TLDR
A possible mechanism for the formation of p-cresol from menthofuran has been proposed on the basis of both in vivo and in vitro studies.
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It is demonstrated that p-cresol is the most toxic cResol isomer in rat liver tissue and that its toxicity is dependent on the formation of a reactive intermediate, and the mechanism(s) of toxicity of the o- and m-isomers may differ from that of p- cresol.
THE CARBON MONOXIDE-BINDING PIGMENT OF LIVER MICROSOMES. I. EVIDENCE FOR ITS HEMOPROTEIN NATURE.
  • T. Omura, R. Sato
  • Biology, Chemistry
    The Journal of biological chemistry
  • 1964
TLDR
The present paper gives a detailed account of the investigations on rabbit liver microsomes and crude microsomal digests, which have led to postulate the hemoprotein nature of the pigment.
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