Selective Synthesis of 3--Palmitoyl-Silybin, a New-to-Nature Flavonolignan with Increased Protective Action against Oxidative Damages in Lipophilic Media.

Clicks: 239
ID: 12445
2018
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Abstract
A selective acylation protocol using cerium chloride (CeCl₃) as catalyst was applied to functionalize silybinin (), a natural antioxidant flavonolignan from milk thistle fruit, in order to increase its solubility in lipophilic media while retaining its strong antioxidant activity. The selective esterification of at the position 3-OH with a palmitate acyl chain leading to the formation of the 3--palmitoyl-silybin () was confirmed by both mass spectroscopy (MS) and nuclear magnetic resonance (NMR) analyses. The antioxidant activity of was at least retained and even increased with the CUPRAC assay designed to estimate the antioxidant activity of both hydrophilic and lipophilic compounds. Finally, the 3--palmitoylation of , resulting in the formation of , also increased its anti-lipoperoxidant activity (i.e., inhibition of conjugated diene production) in two different lipophilic media (bulk oil and / emulsion) subjected to accelerated storage test.
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drouet2018selectivemolecules Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Drouet, Samantha;Doussot, Joël;Garros, Laurine;Mathiron, David;Bassard, Solène;Favre-Réguillon, Alain;Molinié, Roland;Lainé, Éric;Hano, Christophe;
Journal molecules
Year 2018
DOI
E2594
URL
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