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

• Type: Article in International Scientific Journal
• Date: 2021

Authors

Lopes, R (Author) Other; Costa, M (Author) Other; Ferreira, M (Author) Other; Paula Gameiro (Author) FCUP; Fernandes, S (Author) Other; Cristina Catarino (Author) FFUP; Alice Santos Silva (Author) FFUP; Fatima Paiva Martins (Author) FCUP

Journal

Title: Biochimica et Biophysica Acta: Biomembranes

Vol. 1863

ISSN: 0005-2736

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 16 Citations

Scopus - 20 Citations

Other information

Authenticus ID: P-00V-AT1

DOI: 10.1016/j.bbamem.2021.183727

Abstract (EN): 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 mu M, 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 mu M, 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9