Abstract
Stilbene metabolites are attracting great interest because many of them exhibit similar or even stronger biological effects than their parent compounds. Furthermore, the metabolized forms are predominant in biological fluids; therefore, their study is highly relevant. After hemisynthesis production, isolation, and structural elucidation, three glucuronide metabolites for oxyresveratrol (ORV) were formed: trans-ORV-4′-O-glucuronide, trans-ORV-3-O-glucuronide, and trans-ORV-2′-O-glucuronide. In addition, two glucuronide metabolites were obtained for gnetol (GN): trans-GN-2′-O-glucuronide and trans-GN-3-O-glucuronide. When the metabolism of ORV and GN is studied in vitro by human and rat hepatic enzymes, four of the five hemisynthesized compounds were identified and quantified. Human enzymes glucuronidated preferably at the C-2′ position, whereas rat enzymes do so at the C-3 position. In view of these kinetic findings, rat enzymes have a stronger metabolic capacity than human enzymes. Finally, ORV, GN, and their glucuronide metabolites (mainly at the C-3 position) decreased nitric oxide, reactive oxygen species, interleukin 1β, and tumor necrosis factor α production in lipopolysaccharide-stimulated macrophages.
Highlights
Oxyresveratrol (ORV, trans-2′,3,4′,5-tetrahydroxystilbene) and gnetol (GN, trans-2′,3,5,6′-tetrahydroxystilbene) are stilbene monomers that are structurally very similar to resveratrol
Incubated with ORV, GN, and their glucuronide metabolites (5−200 μM) in RPMI medium supplemented with glutamine (4 mM) in the presence or absence of LPS (0.1 μg/mL) (200 μL final volume per well)
Acetobromo-α-D-glucuronic acid methyl ester (2 equiv) dissolved in 10 mL of ethanol was incorporated in the reaction vial
Summary
Oxyresveratrol (ORV, trans-2′,3,4′,5-tetrahydroxystilbene) and gnetol (GN, trans-2′,3,5,6′-tetrahydroxystilbene) are stilbene monomers that are structurally very similar to resveratrol. Whereas resveratrol is the most widely studied stilbene, a growing body of evidence is showing that GN and ORV have potentially valuable bioactive properties.. Whereas resveratrol is the most widely studied stilbene, a growing body of evidence is showing that GN and ORV have potentially valuable bioactive properties.3 Both are attracting attention for human health, as confirmed by several in vitro and in vivo studies.. ORV has been studied for its antioxidant, antimicrobial, antifungal, anti-inflammatory, and neuroprotective properties It prevented amyloid β25−35-induced neuronal cell damage in rat cortical neurons by attenuating the increase in cytosolic Ca2+ levels and the release of glutamate and reducing reactive oxygen species (ROS)..
Sign-in/Register to view highlights & summary Sign-in/Register to access full text options 
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call
