Evidence for the formation of a known toxin, p-cresol, from menthofuran.
Menthofuran (II, 4,5,6,7-tetrahydro-3,6-dimethyl benzofuran), the proximate toxin of R-(+)-pulegone (I), was administered orally to rats (200 mg/kg of body weight/day) for three days and the urinary metabolites were investigated. Among the several metabolites formed, two of them viz. 4-Hydroxy-4-methyl-2-cyclohexenone (VII) and p-cresol (VIII) were identified. In support of the formation of these metabolites, it has been demonstrated that phenobarbital induced rat liver microsomes readily convert 4-methyl-2-cyclohexenone (V) to 4-hydroxy-4-methyl-2-cyclohexenone (VII) and p-cresol (VIII) in the presence of NADPH and O2. Possible mechanism for the formation of these two metabolites (VII, VIII) from menthofuran (II) has been proposed.
Madyastha
K M
KM
Department of Organic Chemistry, Indian Institute of Science, Bangalore.
Raj
C P
CP
D000818:Animals; D001711:Biotransformation; D003408:Cresols / Q000302:isolation & purification / Q000378:metabolism* / Q000652:urine; D008401:Gas Chromatography-Mass Spectrometry; D008297:Male; D008862:Microsomes, Liver / Q000378:metabolism*; D039821:Monoterpenes; D051381:Rats; D011919:Rats, Inbred Strains; D013729:Terpenes / Q000378:metabolism*
D003408:Cresols; D039821:Monoterpenes; D013729:Terpenes; C032538:4-cresol; C054487:menthofuran