Studies on the metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat: isolation and characterization of new metabolites.
1. The metabolic disposition of R-(+)-pulegone (I) was examined in rats following four daily oral doses (250 mg/kg). 2. Six metabolites, namely pulegol (II), 2-hydroxy-2-(1-hydroxy-1-methylethyl)-5-methylcyclohexanone (III), 3,6-dimethyl-7a-hydroxy-5,6,7,7a-tetrahydro-2(4H)-benzofuranone (IV), menthofuran (V), 5-methyl-2-(1-methyl-1-carboxyethylidene)cyclohexanone (VI), and 5-methyl-5-hydroxy-2-(1-hydroxy-1-carboxyethyl)cyclohexanone (VII) have previously been isolated from rat urine, and identified (Moorthy et al. (1989a). Eight new metabolites have now been isolated from rat urine, namely, 5-hydroxy-pulegone (VIII), piperitone (IX), piperitenone (X), 7-hydroxy-piperitone (XI), 8-hydroxy piperitone (XII), p-cresol (XIII), geranic acid (XIV) and neronic acid (XV). These were identified by n.m.r., i.r. and mass spectrometry. 3. Based on these results, metabolic pathways for the biotransformation of R-(+)-pulegone in rat have been proposed.
Madyastha
K M
KM
Department of Organic Chemistry, Indian Institute of Science, Bangalore.
Raj
C P
CP
D000818:Animals; D000081005:Cyclohexane Monoterpenes; D008297:Male; D008610:Menthol / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000652:urine; D039821:Monoterpenes; D051381:Rats
D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D008610:Menthol; C039648:pulegone