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

Madyastha, KM and Gaikwad, NW (1998) Metabolic fate of S-(-)-pulegone in rat. In: Xenobiotica, 28 (08). pp. 723-734.

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Official URL: http://informahealthcare.com/doi/abs/10.1080/00498...

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 O . 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.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Informa plc.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 24 Dec 2009 07:47
Last Modified: 02 May 2011 07:16
URI: http://eprints.iisc.ernet.in/id/eprint/18912

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