Metabolism of a monoterpene ketone, R-(+)-pulegone--a hepatotoxin in rat.
1. R-(+)-Pulegone was administered orally to rats and the urinary metabolites were investigated. Six metabolites were isolated and purified using column and thin layer chromatographic techniques. Metabolites were identified by i.r., n.m.r. and mass spectral analyses. 2. The neutral metabolites isolated from urine of rats treated with pulegone (I) were: pulegone (II), 2-hydroxy-2(1'-hydroxy-1'-methylethyl)-5-methylcyclohexanone (III), 3,6-dimethyl-7a-hydroxy-5,6,7,7a-tetrahydro-2(4H)-benzofuranone (V) and menthofuran (VII). Metabolites II and III were also excreted in conjugated form. 3. Acidic metabolites isolated from urine of rats treated with pulegone (I) were: 5-methyl-2(1'-methyl-1'-carboxyethylidene)cyclohexanone (IV) and 5-methyl-5-hydroxy-2(1'hydroxy-1'-carboxyethyl)cyclohexanone (VI).
Moorthy
B
B
Department of Organic Chemistry, Indian Institute of Science, Bangalore.
Madyastha
P
P
Madyastha
K M
KM
D000284:Administration, Oral; D000818:Animals; D001572:Benzofurans / Q000652:urine; D056486:Chemical and Drug Induced Liver Injury / Q000209:etiology*; D002855:Chromatography, Thin Layer; D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones / Q000652:urine; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D008610:Menthol / Q000031:analogs & derivatives* / Q000378:metabolism / Q000633:toxicity; D039821:Monoterpenes; D051381:Rats
D001572:Benzofurans; D000081005:Cyclohexane Monoterpenes; D003512:Cyclohexanones; D039821:Monoterpenes; D008610:Menthol; C039648:pulegone