Vescalagin and castalagin are two diastereoisomers. The variability of their principal physicochemical properties, compared with their small structural differences, suggests important conformational variations. This study shows, experimentally, that vescalagin has a greater effect on polarity, oxidizability in solution, and thermodegradability than castalagin. Conformational analysis by molecular mechanics demonstrated that vescalagin was more hydrophilic and was more reactive to electrophilic reagents than castalagin. Experimental results were thus explained and demonstrated the distinct behaviors of vescalagin and castalagin. These results were attributed to the C1 position of the two compounds because vescalin and castalin have comparable characteristics. Experimental data were confirmed and interpreted by molecular mechanics. This work represents one of the first attempts to correlate conformation and the properties of phenolic compounds. This step constitutes a predictive method for the pharmacology or chemistry of new compounds.

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Centre d'études structurales et d'analyses des molécules organiques (CESAMO),

This paper introduces a new fractionation method by selective extractions and precipitations making it possible to collect the three groups of oak heartwood extractable polymers in a single operation. The three families, lignins, polysaccharides and ellagitannins, were obtained and each was characterized by different techniques. We grouped together the techniques used to characterize these different oak wood groups of polymers: IR, GC, GC-MS, LC-MS, 1 H NMR, SEC, MALDI-TOF/MS. This work focuses on the qualitative aspect only.