Synthesis, in vitro reactivity, and identification of 6-phenyl-3-hexen-2-one in human urine after kava-kava (Piper methysticum) ingestion

This study describes the synthesis of 6 -phenyl-3-hexen-2-one, a proposed metabolite of kava-kava (kava, 'Awa, Yaqona, Piper methysticum Forst.), its reactivity with glutathione in vitro, and its isolation and identification, as its mercapturic acid adduct using LC/MS/MS, in the urine of two hu...

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Bibliographic Details
Published inPlanta medica Vol. 71; no. 2; pp. 142 - 146
Main Authors Zou, L, Harkey, M.R, Henderson, G.L
Format Journal Article
LanguageEnglish
Published Germany 01.02.2005
Subjects
6-phenyl-3-hexen-2-one
Administration, Oral
Beverages
Chemical and Drug Induced Liver Injury - etiology
chemical reactions
chemical structure
glutathione
hepatotoxicity
herbaceous plants
human health
Humans
Kava
Lactones - urine
Liver - drug effects
Liver - metabolism
phytochemicals
Phytotherapy
Piper methysticum
Piperaceae
plant extracts
Plant Extracts - administration & dosage
Plant Extracts - pharmacology
Plant Extracts - toxicity
Plant Roots
spectral analysis
urine
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Summary:This study describes the synthesis of 6 -phenyl-3-hexen-2-one, a proposed metabolite of kava-kava (kava, 'Awa, Yaqona, Piper methysticum Forst.), its reactivity with glutathione in vitro, and its isolation and identification, as its mercapturic acid adduct using LC/MS/MS, in the urine of two human subjects following their ingestion of kava. A possible metabolic pathway for the formation of this metabolite and its possible role in hepatotoxicity are also discussed.
ISSN:0032-0943
1439-0221
DOI:10.1055/s-2005-837781