Document Detail

Detection of a "nonaromatic" NIH shift during in vivo metabolism of the monoterpene carvone in humans.
MedLine Citation:
PMID:  11879059     Owner:  NLM     Status:  MEDLINE    
High-resolution gas chromatography in combination with mass spectrometry and high-resolution mass spectrometry was used to determine the positions and extent of labeling in the metabolites of carvone, namely in alpha,4-dimethyl-5-oxo-3-cyclohexene-1-acetic acid (dihydrocarvonic acid), alpha-methylene-4-methyl-5-oxo-3-cyclohexene-1-acetic acid (carvonic acid), and 5-(1,2-dihydroxy-1-methylethyl)-2-methyl-2-cyclohexen-1-one (uroterpenolone), after human ingestion of 9,9-dideutero- and 9-(13)C-carvone. Carvonic acid was formed by oxidation at the methyl carbon of the isopropenyl group of carvone, whereas dihydrocarvonic acid was formed by oxidation at the methylene position, most probably via carvone epoxide. A "nonaromatic" NIH shift must occur during the subsequent reactions yielding dihydrocarvonic acid. Additionally, dehydrogenation of dihydrocarvonic acid and hydrogenation of carvonic acid were observed, resulting in minor amounts of both acids owning a carboxy group of opposite origin. Uroterpenolone was found to be exclusively formed by oxidation at the methylene carbon of the isopropenyl group of carvone, and thus, most probably by hydrolysis of carvone epoxide.
Wolfgang Engel
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Journal of agricultural and food chemistry     Volume:  50     ISSN:  0021-8561     ISO Abbreviation:  J. Agric. Food Chem.     Publication Date:  2002 Mar 
Date Detail:
Created Date:  2002-03-06     Completed Date:  2002-04-23     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  0374755     Medline TA:  J Agric Food Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1686-94     Citation Subset:  IM    
Deutsche Forschungsanstalt für Lebensmittelchemie, Lichtenbergstrasse 4, D-85748 Garching, Germany.
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MeSH Terms
Antineoplastic Agents, Phytogenic / chemistry,  metabolism*,  pharmacokinetics
Carbon Isotopes
Chromatography, Gas
Deuterium / diagnostic use
Gas Chromatography-Mass Spectrometry
Terpenes / chemistry,  metabolism*,  pharmacokinetics
Reg. No./Substance:
0/Antineoplastic Agents, Phytogenic; 0/Carbon Isotopes; 0/Monoterpenes; 0/Terpenes; 7782-39-0/Deuterium; 99-49-0/carvone

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