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Interaction of antioxidant biobased epicatechin conjugates with biomembrane models

AutorLázaro, Elisabet; Castillo Expósito, José A.; Ráfols, Clara; Rosés, Martí; Clapés Saborit, Pere
Palabras claveAntioxidants
Catechins
Flavonoids
Liposomes
Artificial membranes
Fecha de publicación27-mar-2007
EditorAmerican Chemical Society
CitaciónJournal of Agriculture and Food Chemistry 55(8): 2901-2905 (2007)
Resumen(-)-Epicatechin conjugates with sulfur-containing moieties are strong free radical scavengers with cell-protecting activities, which may be in part modulated by their capacity to bind to biological membranes. We present here a study of the interaction of these conjugates with membrane models such as multilamellar vesicles and a phospholipid-coated silica column (immobilized artificial membrane), monitored by differential scanning calorimetry and high-performance liquid chromatography, respectively. The nonpolyphenolic moiety significantly influenced the membrane behavior of the whole molecules. Bulky and hydrophobic conjugates clearly interacted with the phospholipids and may have a tendency to penetrate into the hydrophobic core of the vesicles. In contrast, the smaller cationic 4β-(2-aminoethylthio)epicatechin may be located at the outer interface of the lipid membrane. The outcomes from both experimental set-ups were in good agreement. The differences detected in the biological activities of the conjugates may be explained in part by their tendency to penetrate the cell membrane.
Descripción5 pages, 5 figures.-- PMID: 17385884 [PubMed].-- Printed version published on Apr 18, 2007.
Versión del editorhttp://dx.doi.org/10.1021/jf063327d
URIhttp://hdl.handle.net/10261/9881
DOI10.1021/jf063327d
ISSN1520-5118
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