Document Detail


Sulfation of resveratrol in human liver: evidence of a major role for the sulfotransferases SULT1A1 and SULT1E1.
MedLine Citation:
PMID:  16418064     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Sulfation of resveratrol, a polyphenolic compound present in grapes and wine with anticancer and cardioprotective activities, was studied in human liver cytosol. In the presence of 3'-phosphoadenosine-5'-phosphosulfate, three metabolites (M1-3) whose structures were identified by mass spectrometry and NMR as trans-resveratrol-3-O-sulfate, trans-resveratrol-4'-O-sulfate, and trans-resveratrol-3-O-4'-O-disulfate, respectively. The kinetics of M1 formation in human liver cytosol exhibited an pattern of substrate inhibition with a K(i) of 21.3 +/- 8.73 microM and a V(max)/K(m) of 1.63 +/- 0.41 microLmin(-1)mg(-1) protein. Formation of M2 and M3 showed sigmoidal kinetics with about 56-fold higher V(max)/K(m) values for M3 than for M2 (2.23 +/- 0.14 and 0.04 +/- 0.01 microLmin(-1)mg(-1)). Incubation in the presence of human recombinant sulfotransferases (SULTs) demonstrated that M1 is almost exclusively catalysed by SULT1A1 and only to a minor extent by SULT 1A2, 1A3 and 1E1, whereas M2 is selectively formed by SULT1A2. M3 is mainly catalysed by SULT1A2 and 1A3. In conclusion, the results elucidate the enzymatic pathways of resveratrol in human liver, which must be considered in humans following oral uptake of dietary resveratrol.
Authors:
M Miksits; A Maier-Salamon; S Aust; T Thalhammer; G Reznicek; O Kunert; E Haslinger; T Szekeres; W Jaeger
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Xenobiotica; the fate of foreign compounds in biological systems     Volume:  35     ISSN:  0049-8254     ISO Abbreviation:  Xenobiotica     Publication Date:  2005 Dec 
Date Detail:
Created Date:  2006-01-18     Completed Date:  2006-05-03     Revised Date:  2013-06-03    
Medline Journal Info:
Nlm Unique ID:  1306665     Medline TA:  Xenobiotica     Country:  England    
Other Details:
Languages:  eng     Pagination:  1101-19     Citation Subset:  IM    
Affiliation:
Department of Clinical Pharmacy and Diagnostics, University of Vienna, Austria.
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MeSH Terms
Descriptor/Qualifier:
Adolescent
Adult
Aged
Arylsulfotransferase / metabolism*
Chromatography, Liquid
Cytosol / enzymology
Dose-Response Relationship, Drug
Enzyme Inhibitors / metabolism,  pharmacology
Female
Humans
Kinetics
Liver / enzymology*
Magnetic Resonance Spectroscopy
Male
Mass Spectrometry
Middle Aged
Protein Isoforms / metabolism
Recombinant Proteins / metabolism
Stilbenes / metabolism*
Sulfates / chemistry,  metabolism
Sulfotransferases / chemistry,  metabolism*
Chemical
Reg. No./Substance:
0/Enzyme Inhibitors; 0/Protein Isoforms; 0/Recombinant Proteins; 0/Stilbenes; 0/Sulfates; EC 2.8.2.-/Sulfotransferases; EC 2.8.2.1/Arylsulfotransferase; EC 2.8.2.1/SULT1A1 protein, human; EC 2.8.2.1/SULT1A2 protein, human; EC 2.8.2.4/estrone sulfotransferase; Q369O8926L/resveratrol

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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