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Metabolic fate of menthofuran in rats. Novel oxidative pathways

Madyastha, KM and Rajendran, CP (1974) Metabolic fate of menthofuran in rats. Novel oxidative pathways. In: Drug Metabolism and Disposition, 20 (2). pp. 295-301.

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Metabolic fate of menthofuran (II) in rats was investigated. Menthofuran (II) was administered orally (200 mg/kg of the body weight/day) to rats for 3 days. The following metabolites were isolated from the urine of these animals: p-cresol (VI), 5-methyl-2-cyclohexen-1- one (VII), 3-methylcyclohexanone (VIII), 3-methylcyclohexanol (IX), 4- hydroxy-4-methyl-2-cyclohexen-1-one (V), geranic acid (XI), neronic acid (XII), benzoic acid (XIII), and 2-[2'-keto-4'- methylcyclohexyl]propionic acid (X). Incubation of menthofuran (II) with phenobarbital-induced rat liver microsomes in the presence of NADPH and oxygen resulted in the formation of a metabolite tentatively identified as 2-Z-(2'-keto-4'-methylcyclohexylidene)propanal (III; alpha,beta-unsaturated-gamma-keto-aldehyde). The structure assigned was further supported by trapping this metabolite (III) as a cinnoline derivative. Phenobarbital-induced rat liver microsomes also converted 4- methyl-2-cyclohexenone (IV) to 4-hydroxy-4-methyl-2-cyclohexenone (V) and p-cresol (VI) in the presence of NADPH and oxygen. On the basis of both in vivo and in vitro studies, a possible mechanism for the formation of p-cresol from menthofuran has been proposed.

Item Type: Journal Article
Publication: Drug Metabolism and Disposition
Publisher: American Society for Pharmacology and Experimental Therapeutics
Additional Information: Copyright of this article belongs to American Society for Pharmacology and Experimental Therapeutics.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 31 Dec 2009 09:07
Last Modified: 31 Dec 2009 09:07
URI: http://eprints.iisc.ac.in/id/eprint/24665

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