Detection of a "Nonaromatic" NIH shift during in vivo metabolism of the monoterpene carvone in humans

Journal of Agricultural and Food Chemistry

Volumn 50, Issue 6, 2002, Pages 1686-1694

  Engel, Wolfgang ^a  

^a DEUTSCHE FORSCHUNGSANSTALT FÜR LEBENSMITTELCHEMIE   (Germany)

Author keywords

,4 dimethyl 5 oxo 3 cyclohexene 1 acetic acid; methylene 4 methyl 5 oxo 3 cyclohexene 1 acetic acid; 5 (1,2 dihydroxy 1 methylethyl) 2 methyl 2 cyclohexen 1 one; 9,9 dideutero carvone; 9 (13C) carvone; Carvone; MICA; Nonaromatic NIH shift; Urinary metabolites

Indexed keywords

ANTINEOPLASTIC AGENT; CARBON; CARVONE; DEUTERIUM; DIAGNOSTIC AGENT; TERPENE; TERPHENYL DERIVATIVE;

ARTICLE; CHEMISTRY; FOOD COMPOSITION; GAS CHROMATOGRAPHY; GERMANY; HUMAN; HUMAN EXPERIMENT; HYDROLYSIS; MASS FRAGMENTOGRAPHY; MASS SPECTROMETRY; METABOLISM; OXIDATION REDUCTION REACTION; REDUCTION; SYNTHESIS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CARBON ISOTOPES; CHROMATOGRAPHY, GAS; DEUTERIUM; GAS CHROMATOGRAPHY-MASS SPECTROMETRY; HUMANS; HYDROLYSIS; MONOTERPENES; OXIDATION-REDUCTION; TERPENES;

EID: 0037070373     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf011199h     Document Type: Article

References (13)

1. In vivo studies on the metabolism of the monoterpenes S-(+)- and R-(-)-carvone in humans using the metabolism of ingestion-correlated amounts (MICA) approach
2. Transition-state structure variation in the Diels-Alder reaction from secondary deuterium kinetic isotope effects. The reaction of nearly symmetrical dienes and dienophiles is nearly synchronous
3. Terpenoid biotransformation in mammals. V. Metabolism of (+)-citronellal, (±)-7-hydroxy-citronellal, citral, (-)-perillaldehyde, (-)-myrtenal, cuminaldehyde, thujone, and (±)-carvone in rabbits
4. Mass spectrometric analysis. Molecular rearrangements
5. Intramolecular hydrogen transfer in mass spectra. II. McLafferty rearrangement and related reactions
6. Hydroxylation-induced migration. NIH shift
7. The role of arene oxideoxepin systems in the metabolism of aromatic substrates. II. Synthesis of 3,4-toluene-4-d oxide and subsequent "NIH shift" to 4-hydroxytoluene-3-d
8. Deuterium migration during the acid-catalyzed dehydration of 6-deuterio-5,6-dihydroxy-3-chloro-1, 3-cyclohexadiene, a nonenzymatic model for the NIH shift
9. The NIH-shift in the in vivo hydroxylation of ring-deuterated L-phenylalanine in man
10. Isolation of a stable benzene oxide from a fungal biotransformation and evidence for an "NIH shift" of the carbomethoxy group during hydroxylation of methyl benzoates
11. NIH shift in the hydroxylation of aromatic compounds by the ammonia-oxidizing bacterium Nitrosomonas europaea. Evidence against an arene oxide intermediate
12. Rearrangements in the cerium(IV) and manganese(III) oxidations of substituted naphthalenes and the NIH shift mechanism
13. Aromatic hydroxylation mediated by flavin autoxidation. Lack of the NIH shift