| In vivo studies on the metabolism of the monoterpene pulegone in humans using the metabolism of ingestion-correlated amounts (MICA) approach: explanation for the toxicity differences between (S)-(-)- and (R)-(+)-pulegone. | |
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MedLine Citation:
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PMID: 14558782 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The major in vivo metabolites of (S)-(-)-pulegone in humans using a metabolism of ingestion-correlated amounts (MICA) experiment were newly identified as 2-(2-hydroxy-1-methylethyl)-5-methylcyclohexanone (8-hydroxymenthone, M1), 3-hydroxy-3-methyl-6-(1-methylethyl)cyclohexanone (1-hydroxymenthone, M2), 3-methyl-6-(1-methylethyl)cyclohexanol (menthol), and E-2-(2-hydroxy-1-methylethylidene)-5-methylcyclohexanone (10-hydroxypulegone, M4) on the basis of mass spectrometric analysis in combination with syntheses and NMR experiments. Minor metabolites were be identified as 3-methyl-6-(1-methylethyl)-2-cyclohexenone (piperitone, M5) and alpha,alpha,4-trimethyl-1-cyclohexene-1-methanol (3-p-menthen-8-ol, M6). Menthofuran was not a major metabolite of pulegone and is most probably an artifact formed during workup from known (M4) and/or unknown precursors. The differences in toxicity between (S)-(-)- and (R)-(+)-pulegone can be explained by the strongly diminished ability for enzymatic reduction of the double bond in (R)-(+)-pulegone. This might lead to further oxidative metabolism of 10-hydroxypulegone (M4) and the formation of further currently undetected metabolites that might account for the observed hepatotoxic and pneumotoxic activity in humans. |
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Authors:
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Wolfgang Engel |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of agricultural and food chemistry Volume: 51 ISSN: 0021-8561 ISO Abbreviation: J. Agric. Food Chem. Publication Date: 2003 Oct |
Date Detail:
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Created Date: 2003-10-15 Completed Date: 2003-12-11 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 0374755 Medline TA: J Agric Food Chem Country: United States |
Other Details:
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Languages: eng Pagination: 6589-97 Citation Subset: IM |
Affiliation:
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Deutsche Forschungsanstalt für Lebensmittelchemie, Lichtenbergstrasse 4, D-85748 Garching, Germany. wolfgang.engel@lrz.tum.de |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Cresols
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metabolism,
urine Female Gas Chromatography-Mass Spectrometry Humans Hydrolysis Male Monoterpenes / chemistry, metabolism*, toxicity*, urine |
| Chemical | |
Reg. No./Substance:
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0/Cresols; 0/Monoterpenes; 106-44-5/4-cresol; 15932-80-6/pulegone; 494-90-6/menthofuran |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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