Evidence for the formation of a known toxin, p-cresol, from menthofuran.

Abstract

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.

• Authors: K M Madyastha, C P Raj
• Journal: Biochemical and biophysical research communications (Biochem Biophys Res Commun) Vol. 177 Issue 1 Pg. 440-6 (May 31 1991) ISSN: 0006-291X [Print] United States
• PMID: 2043129 (Publication Type: Journal Article)

Chemical References

• Cresols
• Monoterpenes
• Terpenes
• 4-cresol
• menthofuran

Topics

• Animals
• Biotransformation
• Cresols (isolation & purification, metabolism, urine)
• Gas Chromatography-Mass Spectrometry
• Male
• Microsomes, Liver (metabolism)
• Monoterpenes
• Rats
• Rats, Inbred Strains
• Terpenes (metabolism)