Evaluation of Polyphenolic Acid Esters as Potential Antioxidants

• Published in: Biological & Pharmaceutical Bulletin Vol. 28; no. 7; pp. 1211 - 1215
• Main Authors: Hsu, Ling-Yih, Lin, Chi-Fu, Hsu, Wen-Chuan, Hsu, Wen-Lin, Chang, Tsu-Chung
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 01.07.2005; Pharmaceutical Society of Japan; Japan Science and Technology Agency
• Subjects: antioxidant; Antioxidants - pharmacology; caffeic acid analogue; Drug Evaluation, Preclinical; Esters; Flavonoids - pharmacology; Free Radical Scavengers - pharmacology; free radical scavenging activity; Magnetic Resonance Spectroscopy; Peroxynitrous Acid - chemistry; Phenols - pharmacology; polyphenolic acid ester; Polyphenols
• ISSN: 0918-6158; 1347-5215
• DOI: 10.1248/bpb.28.1211

Six polyphenolic acid esters were synthesized and their antioxidative properties were evaluated in three model systems [2,2′-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging assay, 2,2′-azobis(2-amidinopropane)dihydrochloride (AAPH)-induced lipid peroxidation system, and the dye-bleaching assay of peroxynitrite radical]. Among these compounds, we found that compounds 4 [3,4-dihydroxy-benzoic acid-(2-phenoxyethyl ester)], and 5 [3,4-dihydroxy-cinnamic acid-(2-phenoxyethyl ester)] provided comparable activity to caffeic acid phenethyl ester (CAPE) in the DPPH model. Compound 3 [2,5-dihydroxy-benzoic acid-(2-phenoxyethyl ester)], was found to be more active than CAPE in the AAPH system, it also displayed about 2-fold greater activity than CAPE in the peroxynitrite radical model. These results suggest that these phenolic acid ester derivatives, with their potent anti-oxidant activities, may have useful applications as antioxidants.