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|Title:||Conformational analysis: a tool for the elucidation of the antioxidant properties of ferulic acid derivatives in membrane models.||Authors:||Anselmi, Cecilia
LA ROSA, Caterina
MAFFEI FACINO, R
|Keywords:||Conformational analysis; Antioxidant/radical scavenging activity; Acellular and cellular models; Alkyl ferulates; Ferulic acid||Issue Date:||2004||Project:||None||Journal:||JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS||Abstract:||
With the aim to search and design more effective and safe antioxidant molecules to be used as functional ingredients incosmetic formulations for UV protection, we evaluated the antioxidant/radical scavenging activities of ferulic acid and of somealkyl ferulates in both acellular and cellular systems. Ferulic acid esters, equipotent as antioxidant in homogeneous phase, showedwhen tested in membranous systems (rat liver microsomes, rat erythrocytes) marked differences in antioxidant potency. Then-C12 derivative was the most potent, followed by n-C8, n-C16 and branched C8, and then by ferulic acid.A conformational study carried out by NMR and modelling, indicates that the different antioxidant activity of ferulates inmembrane models is due to the different spatial conformation and arrangement of the side chain of the molecule, which governsthe access and binding to the phospholipid bilayer, the modality of orientation of the scavenging/quenching nucleus (phenolmoiety), and hence the overall antioxidant potency of the derivative.These results emphasize the need of analytical studies (NMR and molecular modelling) addressed to the knowledge of theconformational parameters in combination with conventional antioxidant testings for understanding the antioxidant behaviourof a molecule in a biological membrane/system.
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