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Quantification of free and protein‐bound trans ‐resveratrol metabolites and identification of trans ‐resveratrol‐C/O‐conjugated diglucuronides – Two novel resveratrol metabolites in human plasma
Author(s) -
Burkon Alexander,
Somoza Veronika
Publication year - 2008
Publication title -
molecular nutrition and food research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.495
H-Index - 131
eISSN - 1613-4133
pISSN - 1613-4125
DOI - 10.1002/mnfr.200700290
Subject(s) - chemistry , glucuronide , urine , resveratrol , polyphenol , metabolism , high performance liquid chromatography , metabolite , glycoside , chromatography , biochemistry , stereochemistry , antioxidant
The polyphenol trans ‐resveratrol (t‐RES) is present as t‐RES‐3‐ O ‐β‐ D ‐glycoside, termed piceid, in several plant‐derived foods. Although data on the metabolism and on in vivo effects of t‐RES have been reported, quantitative data on the metabolites formed after dietary intake of t‐RES or piceid are still lacking. In this study, 85.5 mg of piceid per 70 kg of body weight (bw) were administered to healthy volunteers in a bolus dose. t‐RES metabolites formed in plasma and urine were identified and quantified by LC‐MS/MS, NMR, and HPLC‐DAD analysis using chemically synthesized t‐RES conjugate standards. In addition, the amount of t‐RES metabolites bound noncovalently to plasma proteins was determined for the first time in humans. The metabolites identified and quantified were t‐RES‐3‐sulfate, t‐RES‐3,4′‐disulfate, t‐RES‐3,5‐disulfate, t‐RES‐3‐glucuronide and t‐RES‐4′‐glucuronide, with t‐RES‐sulfates being the dominant conjugates in plasma and urine. Besides these metabolites, two novel t‐RES‐C/O‐conjugated diglucuronides have been identified and quantified in plasma and urine. Moreover, it could be shown that up to 50% of the plasma t‐RES‐3‐sulfate, t‐RES‐disulfates, and the novel t‐RES‐C/O‐diglucuronides were bound to proteins. Total recovery of the dietary administered piceid in urine ranged between 13.6 and 35.7%.