Document Detail


Metabolic fate of menthofuran in rats. Novel oxidative pathways.
MedLine Citation:
PMID:  1352224     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Metabolic fate of menthofuran (II) in rats was investigated. Menthofuran (II) was administered orally (200 mg/kg of the body weight/day) to rats for 3 days. The following metabolites were isolated from the urine of these animals: p-cresol (VI), 5-methyl-2-cyclohexen-1-one (VII), 3-methylcyclohexanone (VIII), 3-methylcyclohexanol (IX), 4-hydroxy-4-methyl-2-cyclohexen-1-one (V), geranic acid (XI), neronic acid (XII), benzoic acid (XIII), and 2-[2'-keto-4'-methylcyclohexyl]propionic acid (X). Incubation of menthofuran (II) with phenobarbital-induced rat liver microsomes in the presence of NADPH and oxygen resulted in the formation of a metabolite tentatively identified as 2-Z-(2'-keto-4'-methylcyclohexylidene)propanal (III; alpha,beta-unsaturated-gamma-keto-aldehyde). The structure assigned was further supported by trapping this metabolite (III) as a cinnoline derivative. Phenobarbital-induced rat liver microsomes also converted 4-methyl-2-cyclohexenone (IV) to 4-hydroxy-4-methyl-2-cyclohexenone (V) and p-cresol (VI) in the presence of NADPH and oxygen. On the basis of both in vivo and in vitro studies, a possible mechanism for the formation of p-cresol from menthofuran has been proposed.
Authors:
K M Madyastha; C P Raj
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Drug metabolism and disposition: the biological fate of chemicals     Volume:  20     ISSN:  0090-9556     ISO Abbreviation:  Drug Metab. Dispos.     Publication Date:    1992 Mar-Apr
Date Detail:
Created Date:  1992-08-06     Completed Date:  1992-08-06     Revised Date:  2003-11-14    
Medline Journal Info:
Nlm Unique ID:  9421550     Medline TA:  Drug Metab Dispos     Country:  UNITED STATES    
Other Details:
Languages:  eng     Pagination:  295-301     Citation Subset:  IM    
Affiliation:
Department of Organic Chemistry, Indian Institute of Science, Bangalore.
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MeSH Terms
Descriptor/Qualifier:
Animals
Male
Microsomes, Liver / metabolism*
Monoterpenes*
Phenobarbital / pharmacology
Rats
Terpenes / metabolism*,  urine
Chemical
Reg. No./Substance:
0/Monoterpenes; 0/Terpenes; 494-90-6/menthofuran; 50-06-6/Phenobarbital

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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