Gewählte Publikation:

Miksits, M; Sulyok, M; Schuhmacher, R; Szekeres, T; Jäger, W.
(2009): In-vitro sulfation of piceatannol by human liver cytosol and recombinant sulfotransferases.
J Pharm Pharmacol. 2009; 61(2):185-191 FullText FullText_BOKU

Abstract:

Objectives The aim of this study was to investigate the concentration-dependent sulfation of piceatannol. a dietary polyphenol present in grapes and wine and known for its promising anticancer and anti-inflammatory activity. Methods Sulfation of piceatannol was investigated in human liver cytosol as well as using a panel of recombinant sulfotransferase isoforms. Furthermore, the chemical structures Of novel sulfates were identified by liquid chromatography/mass spectrometry (LC/MS.). Key findings In the presence of 3'-phosphoaedenosine-5'-phosphosulfate, three metabolites could be detected whose structures were identified by LC/MS/MS as piceatannol distillate (M 1) and two monosulfates (M2, M3). The kinetics of M1 formation exhibited I pattern Of Substrate inhibition with a K-i of 21.8 +/- 11.3 mu M and a V-max/K-m of 7.63 +/- 1.80 mu l/mg protein per min. Formation of M2 and M3 showed sigmoidal kinetics with apparent K-m and V-max values of 27.1 +/- 2.90 mu m and 118.4 +/- 4.38 pmol/mg protein per min, respectively, for M2 and 35.7 +/- 2.70 mu m and 81.8 +/- 2.77 pmol/mg protein per min, respectively, for M3. Incubation in the presence of human recombinant sulfotransferases (SULTs) demonstrated that M1 was formed equally by SUUFIA1*1 and SULT1B1 and to a lesser extent by SULT1A1*2. M2 was preferentially catalysed by SULT1A1*2, 1A3 and 1E1. The formation of M3, however, was mainly catalysed by SULT1A2*1 and SULT1A3. Conclusions Our results elucidate the importance of piceatannol sulfation in human liver, which must be taken into account ill humans after dietary intake of piceatannol.

Autor*innen der BOKU Wien:

Schuhmacher Rainer

Sulyok Michael

Find related publications in this database (using NML MeSH Indexing)

Administration, Oral -

Arylsulfotransferase - metabolism

Chromatography, High Pressure Liquid - methods

Cytosol - chemistry

Dietary Supplements -

Dose-Response Relationship, Drug -

Flavonoids - chemistry

Hepatocytes - metabolism

Humans -

Kinetics -

Mass Spectrometry - methods

Molecular Structure -

Phenols - chemistry

Phosphoadenosine Phosphosulfate - metabolism

Recombinant Proteins - chemistry

Stilbenes - chemistry

Sulfates - metabolism

Sulfotransferases - chemistry

Find related publications in this database (Keywords)

liver

piceatannol

sulfation

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