Anti-Oxidative Effects of Pyrogollol Lipid Derivatives on the Oxidation of Unilamellar Vesicles and Rat Blood Plasma
Amphipathic pyrogallol lipid derivatives (PD) containing different carbon atomic length alkyl chains, including –H, –C5H11, –C10H21, –C15H31, and –C20H41 in the C-4 position of the benzene ring were synthesized. 4-Decylpyrogallol displayed contact hypersensitivity, but other compounds did not induce an allergic reaction when rat ears were sensitized with the compounds daily for 10 days. PDs containing more than five carbon atoms in the alkyl chain showed high lipophilicity in n-octanol/ water partition experiments and high rate of incorporation to liposome membranes. In addition, PDs showed higher radical-scavenging activity on 1,1-diphenyl-2-picrylhydrazyl than α-tocopherol and 3-pentylcatechol. PDs efficiently inhibited lipid peroxidation of egg yolk phosphatidyl choline large unilamellar vesicle liposomes induced by lipid- and aqueous-soluble radical generators. Moreover, PDs attenuated the formation of cholesteryl ester hydroperoxides in rat blood plasma induced by copper ions. These results suggest that non-allergenic PDs may act as potent antioxidants against the oxidative damage of cellular and subcellular membranes.
Jae-Hak Moon Jong Hoon Jeong, Jeong-Yong Cho, Hang Yeon Jeong and Hyoung Jae Lee