Interaction of Antioxidant Biobased Epicatechin Conjugates with Biomembrane Models

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• 作者：Elisabet Lá ; zaro ; José ; A. Castillo ; Clara Rá ; fols ; Mart&iacute ; Rosé ; s ; Pere Clapé ; s ; Josep Llu&iacute ; s Torres
• 刊名：Journal of Agricultural and Food Chemistry
• 出版年：2007
• 出版时间：April 18, 2007
• 年：2007
• 卷：55
• 期：8
• 页码：2901 - 2905
• 全文大小：108K
• 年卷期：v.55,no.8(April 18, 2007)
• ISSN：1520-5118

文摘

(-)-Epicatechin conjugates with sulfur-containing moieties are strong free radical scavengers withcell-protecting activities, which may be in part modulated by their capacity to bind to biologicalmembranes. We present here a study of the interaction of these conjugates with membrane modelssuch as multilamellar vesicles and a phospholipid-coated silica column (immobilized artificialmembrane), monitored by differential scanning calorimetry and high-performance liquid chromatography, respectively. The nonpolyphenolic moiety significantly influenced the membrane behavior ofthe whole molecules. Bulky and hydrophobic conjugates clearly interacted with the phospholipidsand may have a tendency to penetrate into the hydrophobic core of the vesicles. In contrast, thesmaller cationic 4-(2-aminoethylthio)epicatechin may be located at the outer interface of the lipidmembrane. The outcomes from both experimental set-ups were in good agreement. The differencesdetected in the biological activities of the conjugates may be explained in part by their tendency topenetrate the cell membrane.