Quantitative NMR analysis of a sesamin catechol metabolite in human urine.
Sesamin, the major sesame oil lignan, is recognized for its health-promoting effects, including the lowering of cholesterol and elevation of gamma-tocopherol in rats and humans. However, little is known about the absorption and metabolism of sesamin in humans. In this study, 6 healthy volunteers took a single dose of sesame oil (508 micromol sesamin) and their urine was collected for four 12-h periods. The urine samples were treated with beta-glucuronidase/sulphatase and extracted with chloroform. The major urinary sesamin metabolite in the chloroform extract was collected using HPLC diode array detector and characterized as (1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo-[3,3,0]octane using NMR and mass spectroscopy. A quantitative (1)H-NMR technique, based on the methylenedioxyphenyl protons signal (delta 5.91), was used for the quantification of the metabolite in the chloroform extracts of urine. The excretion of the sesamin catechol metabolite ranged from 22.2 to 38.6% (mean +/- SD, 29.3 +/- 5.6) of the ingested dose and happened mainly in the 1st 12 h after ingestion.
Moazzami
Ali A
AA
Department of Food Sciences, Swedish University of Agricultural Sciences, S-750 07 Uppsala, Sweden. ali.moazzami@lmv.slu.se
Andersson
Rolf E
RE
Kamal-Eldin
Afaf
A
D000328:Adult; D002396:Catechols / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004149:Dioxoles / Q000378:metabolism* / Q000652:urine*; D004305:Dose-Response Relationship, Drug; D005260:Female; D006801:Humans; D017705:Lignans / Q000378:metabolism* / Q000652:urine*; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D013058:Mass Spectrometry; D009795:Octanes / Q000378:metabolism / Q000652:urine*; D010865:Pilot Projects; D012715:Sesame Oil / Q000008:administration & dosage / Q000378:metabolism; D013997:Time Factors
C519254:(1R,2S,5R,6S)-6-(3,4-dihydroxyphenyl)-2-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo-(3,3,0)octane; D002396:Catechols; D004149:Dioxoles; D017705:Lignans; D009795:Octanes; D012715:Sesame Oil; C034221:catechol; C054125:sesamin