MetaboLights
A stilbenol that is 1,1'-ethane-1,2-diyldibenzene with hydroxy groups at positions 1, 3 and 4'.
Identification
5-[2-(4-hydroxyphenyl)ethyl]benzene-1,3-diol
3,4',5-trihydroxybibenzyl
Europe PubMed Central results
Determination of dihydroresveratrol in rat plasma by HPLC.
Author: Juan ME, Alfaras I, Planas JM.
Abstract: Dihydroresveratrol is a metabolite of trans-resveratrol formed in the intestine by the hydrogenation of the double bond by microflora. The aim of the present study was to validate a method to measure dihydroresveratrol in rat plasma and then to quantify its plasmatic concentration after the oral administration of 60 mg/kg to Sprague-Dawley rats. Dihydroresveratrol was extracted from acidified plasma with a C18 cartridge, eluted with methanol, and concentrated prior to HPLC analysis with diode-array detection (HPLC-DAD) at 276 nm. The method was validated by spiking blank plasma samples with pure dihydroresveratrol, obtaining a linear correlation and good interday and intraday precisions, expressed as coefficient of variation (<7%). The average recovery was 96.7% and the limit of detection was 275 nM. The oral administration of dihydroresveratrol to rats and its subsequent detection, along with dihydroresveratrol glucuronide and sulfate, provides evidence of its absorption and metabolism.
DOI: 10.1021/jf100836j
Resveratrol, but not dihydroresveratrol, induces premature senescence in primary human fibroblasts.
Author: Faragher RG, Burton DG, Majecha P, Fong NS, Davis T, Sheerin A, Ostler EL.
Abstract: Resveratrol, trans-3,5,4'-trihydroxystilbene, is a polyphenolic compound which has been reported to mimic the gene expression patterns seen in whole animals undergoing dietary restriction. The mechanism of action of resveratrol remains poorly understood, but modulation of both cellular proliferation and apoptosis has been proposed as important routes by which the molecule may exert its effects. This study reports the effects of both resveratrol and dihydroresveratrol (a primary in vivo metabolite) on the proliferative capacity of human primary fibroblasts. No generalised reduction in the growth fraction was observed when fibroblasts derived from three different tissues were treated with resveratrol at concentrations of 10 μm or less. However, concentrations above 25 μm produced a dose-dependent reduction in proliferation. This loss of the growth fraction was paralleled by an increase in the senescent fraction as determined by staining for senescence associated beta galactosidase and dose recovery studies conducted over a 7-day period. Entry into senescence in response to treatment with resveratrol could be blocked by a 30-min preincubation with the p38 MAP kinase inhibitor SB203580. No effects on proliferation were observed when cells were treated with dihydroresveratrol at concentrations of up to 100 μm.
Pharmacokinetics of resveratrol metabolic profile in healthy humans after moderate consumption of red wine and grape extract tablets.
Author: Rotches-Ribalta M, Andres-Lacueva C, Estruch R, Escribano E, Urpi-Sarda M.
Abstract: A pharmacokinetic study of the metabolic profile of resveratrol has been performed in healthy men after moderate red wine (RW) consumption. The bioavailability of resveratrol is highly influenced by several factors such as the food matrix and, therefore, this study has been compared with a pilot study in which men ingested grape extract (GE) tablets as a nutraceutical, containing similar total amounts of resveratrol than RW. Blood and urine samples were taken before and at several time points after intervention and then analyzed by SPE and LC-ESI-MS/MS. Up to 17 resveratrol and piceid derivatives were identified, including those formed by the intestinal microbiota. Resveratrol glucosides were found in plasma as intact forms and reached the lowest maximum concentrations 1h after both interventions. Higher plasma concentrations and longer times (t(max)) were observed for resveratrol glucuronides due to phase II metabolism and even higher values for conjugates derived from microbiota, such as dihydroresveratrol-glucuronides. The same trend was observed for total excreted amounts in urine samples. When both treatments were compared, statistically significant differences for some metabolites were obtained, which may be due to the different composition of resveratrol and piceid in both sources. However, GE formulation seems to delay resveratrol absorption, staying longer in the gut where could be metabolized to a greater degree, since 2.1-3.6-fold higher urinary concentrations of microbial metabolites were observed after GE intervention at 12-24h urinary fraction. Therefore, supplement intake could be also a way to bring resveratrol benefits to human health.
Matrix effects on the bioavailability of resveratrol in humans
Author: Ortuño J, Covas MI, Farre M, Pujadas M, Fito M, Khymenets O, Andres-Lacueva C, Roset P, Joglar J, Lamuela-Raventós RM, Torre Rdl.
Abstract: The pharmacokinetics of resveratrol in 11 healthy male volunteers has been assessed in a randomized, crossover, controlled clinical trial after the administration of three grape products: red wine (250mL), grape juice (1/L), or tablets (red wine extracts enriched with trans-resveratrol). Doses of trans-resveratrol independently of the product administered, were about 14μg/kg. Biological samples were collected and analysed by capillary gas chromatography-mass spectrometry. cis-Resveratrol, trans-resveratrol and dihydroresveratrol were determined in plasma and urine. Plasma concentration of trans-resveratrol after hydrolysis increased as a response to all grape products and that of cis-resveratrol after wine and grape juice. Free forms of these phenolic compounds were deemed undetectable in plasma. Despite similar trans-resveratrol doses being administered, its bioavailability from wine and grape juice was 6-fold higher, than that from tablets. Resveratrol was better absorbed from natural grape products than from tablets, pointing out the importance of the matrix in its bioavailability.