(6 R)- (+)-Menthofuran, a minor constituent of peppermint and cornmint oils, is a major metabolite of (1R )- (+)-β-pulegone. It is hepatotoxic because it destroys CYP enzymes, as does pulegone (see Constituent profiles, Chapter 14 ). Unlike pulegone, menthofuran does not deplete glutathione ( Thomassen et al 1990 ).How is menthofuran made from pulegone?
Menthofuran is produced biosynthetically from pulegone by the enzyme menthofuran synthase . Menthofuran can be synthesized from 5-methylcyclohexane-1,3-dione and allenyldimethylsulfonium bromide in two steps via a furannulation strategy consisting of enolate addition and rearrangement.What is the mechanism of action of menthofuran?
PubMed: (R)- (+)-Menthofuran is a potent, mechanism-based inactivator of human liver cytochrome P450 2A6. PubMed: Multiple organ failure after ingestion of pennyroyal oil from herbal tea in two infants.Is menthofuran a monoterpenoid?
More... Menthofuran is a monoterpenoid that is 4,5,6,7-tetrahydro-1-benzofuran substituted by methyl groups at positions 3 and 6. It has a role as a nematicide and a plant metabolite. It is a member of 1-benzofurans and a monoterpenoid.