Metabolic fate of S-(-)-pugelone in rat

K. M. Madyastha, Nilesh W. Gaikwad

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

1. S-(-)-pulegone was administered orally to rat (250 mg/kg) and the nature of the urinary metabolites was investigated. Eleven metabolites, namely S-(-)-menthofuran, piperitone, piperitenone, p-cresol, 5-hydroxypulegone, 4-methylcyclohexenone, 3-methylcyclohexanone, isopulegone, pulegol, 7-hydroxypiperitone and benzoic acid, have been isolated from rat urine. It is assumed that menthofuran, isopulegone and 4-methylcyclohexenone retain the stereochemistry of the parent compound, whereas in other metabolites the stereochemistry at the asymmetric centres is not known. 2. The relative amounts of various major metabolites present in the total urine extracts from the R-(+) and S-(-)-pulegone-treated rat were established by glc analyses. Urine samples of rats treated with R-(+)-pulegone contained higher levels of p-cresol and piperitenone than in similar experiment carried out with S-(-)-pulegone, whereas the levels of unmetabolized pulegone, piperitone and benzoic acid were considerably higher in the urine of rat treated with S-(-)-pulegone than in a corresponding experiment with R-(+)-pulegone. 3. Phenobarbital-induced rat liver microsomes converted S-(-)-pulegone to S-(-)-menthofuran (VII) and piperitenone (III) in the presence of NADPH and O2. The levels of VII and III were significantly higher in similar experiments carried out with R-(+)pulegone. 4. 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.

Original languageEnglish (US)
Pages (from-to)723-734
Number of pages12
JournalXenobiotica
Volume28
Issue number8
StatePublished - 1998
Externally publishedYes

Fingerprint

Rats
Metabolites
Urine
Stereochemistry
Benzoic Acid
pulegone
Enantiomers
Experiments
Liver Microsomes
Phenobarbital
Biotransformation
Metabolic Networks and Pathways
NADP
Liver
Toxicity

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)
  • Biochemistry
  • Pharmacology
  • Toxicology
  • Health, Toxicology and Mutagenesis

Cite this

Madyastha, K. M., & Gaikwad, N. W. (1998). Metabolic fate of S-(-)-pugelone in rat. Xenobiotica, 28(8), 723-734.

Metabolic fate of S-(-)-pugelone in rat. / Madyastha, K. M.; Gaikwad, Nilesh W.

In: Xenobiotica, Vol. 28, No. 8, 1998, p. 723-734.

Research output: Contribution to journalArticle

Madyastha, KM & Gaikwad, NW 1998, 'Metabolic fate of S-(-)-pugelone in rat', Xenobiotica, vol. 28, no. 8, pp. 723-734.
Madyastha KM, Gaikwad NW. Metabolic fate of S-(-)-pugelone in rat. Xenobiotica. 1998;28(8):723-734.
Madyastha, K. M. ; Gaikwad, Nilesh W. / Metabolic fate of S-(-)-pugelone in rat. In: Xenobiotica. 1998 ; Vol. 28, No. 8. pp. 723-734.
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