Caffeic acid phenolipids in the protection of cell membranes from oxidative injuries: interaction with the membrane phospholipid bilayer

Rafaela Lopes, Marlene Costa, Mariana Ferreira, Paula Gameiro, Sara Fernandes, Cristina Catarino, Alice Santos-Silva, Fátima Paiva-Martins*

*Autor correspondente para este trabalho

Resultado de pesquisarevisão de pares

12 Citações (Scopus)

Resumo

Caffeic acid (CA) has demonstrated a strong intracellular antioxidant ability by scavenging ROS, contributing to the maintenance of cell membrane structural integrity and to reduce oxidative injuries in other cell components. Nevertheless, caffeic acid has limited usage, due to its hydrophilic character. In this work, the introduction of alkyl chains in the caffeic acid molecule by esterification (methyl - C1, ethyl - C2, butyl - C4, hexyl - C6, octyl - C8 and hexadecyl - C16), significantly increased its lipophilicity. All caffeates tested showed a much higher protective activity than caffeic acid against red blood cells (RBCs) AAPH-induced oxidative stress; this protection was heavily dependent on the length of the alkyl chain of the esters, and on their concentration. At 2.5 and 5 μM, the more lipophilic compounds (C8 and C16) showed a remarkable antioxidant activity, inhibiting hemolysis; probably, their better location within the membrane leads to a better antioxidative protection; however, at 50 μM, the more hydrophilic compounds (C1-C4) showed a better activity against hemolysis than the more lipophilic ones (C8-C16). At this higher concentration, the better interaction of the more lipophilic compounds with the membrane seems to cause changes in RBC membrane fluidity, disturbing membrane integrity. Our data show that the antioxidant activity of these compounds could play an important role for the protection of different tissues and organs, by protecting cell membranes from oxidative injuries.
Idioma originalEnglish
Número do artigo183727
Páginas (de-até)1-9
Número de páginas9
RevistaBiochimica et Biophysica Acta - Biomembranes
Volume1863
Número de emissão12
DOIs
Estado da publicaçãoPublicado - 1 dez. 2021
Publicado externamenteSim

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