ArticleJournal of enzyme inhibition and medicinal chemistry2017
Structure-activity relationships of fraxamoside as an unusual xanthine oxidase inhibitor.
Article in Journal of enzyme inhibition and medicinal chemistry, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed.
- Hydroxytyrosol Modulates Arachidonic Acid Metabolism and Purine Catabolism in Individuals with Prediabetes: An Untargeted Metabolomics Study in a Randomized Controlled Trial.Antioxidants (Basel, Switzerland) · 2026Article
- Structure-Activity Relationships and Changes in the Inhibition of Xanthine Oxidase by Polyphenols: A Review.Foods (Basel, Switzerland) · 2024Review
- Effect of Hydroxytyrosol Derivatives of Donepezil on the Activity of Enzymes Involved in Neurodegenerative Diseases and Oxidative Damage.Molecules (Basel, Switzerland) · 2024Article
- Novel Reversible Inhibitors of Xanthine Oxidase Targeting the Active Site of the Enzyme.Antioxidants (Basel, Switzerland) · 2023Article
- Improvement of Phenolic Compound Extraction by Using Ion Exchange Chromatography and Evaluation of Biological Activities of Polyphenol-enriched Fraction ofIranian journal of pharmaceutical research : IJPR · 2022Article
- DNA protection, antioxidant and xanthine oxidase inhibition activities of polyphenol-enriched fraction ofIranian journal of basic medical sciences · 2018Article
Corrections and comments
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Authors and funding
5 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Fraxamoside, a macrocyclic secoiridoid glucoside featuring a hydroxytyrosol group, was recently identified as a xanthine oxidase inhibitor (XOI) comparable in potency in vitro to the standard antigout drug allopurinol. However, this activity and its considerably higher value than its derivatives oleuropein, oleoside 11-methyl ester, and hydroxytyrosol are not explained by structure-activity relationships (SARs) of known XOIs. To exclude allosteric mechanisms, we first determined the inhibition kinetic of fraxamoside. The resulting competitive mechanism prompted a computational SAR characterization, combining molecular docking and dynamics, which fully explained the behavior of fraxamoside and its derivatives, attributed the higher activity of the former to conformational properties of its macrocycle, and showed a substantial contribution of the glycosidic moiety to binding, in striking contrast with glycoside derivatives of most other XOIs. Overall, fraxamoside emerged as a lead compound for a new class of XOIs potentially characterized by reduced interference with purine metabolism.
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