Synthesis of Selenium-Containing Polyphenolic Acid Esters and Evaluation of Their Effects on Antioxidation and 5-Lipoxygenase Inhibition

• Published in: Chemical & pharmaceutical bulletin Vol. 53; no. 11; pp. 1402 - 1407
• Main Authors: Lin, Chi-Fu, Chang, Tsu-Chung, Chiang, Chih-Chia, Tsai, Hou-Jen, Hsu, Ling-Yih
• Format: Journal Article
• Language: English
• Published: TOKYO The Pharmaceutical Society of Japan 01.11.2005; Pharmaceutical Soc Japan; Japan Science and Technology Agency
• Subjects: 5-lipoxygenase inhibition; antioxidant; Antioxidants - chemical synthesis; Antioxidants - pharmacology; Biphenyl Compounds; Caffeic Acids - chemistry; Caffeic Acids - pharmacology; Chemistry; Chemistry, Medicinal; Chemistry, Multidisciplinary; Flavonoids - chemical synthesis; Flavonoids - pharmacology; free radical scavenging activity; Indicators and Reagents; Kinetics; Life Sciences & Biomedicine; Lipoxygenase Inhibitors - chemical synthesis; Lipoxygenase Inhibitors - pharmacology; organoselenium compound; Oxidation-Reduction; Peroxynitrous Acid - chemistry; Pharmacology & Pharmacy; Phenols - chemical synthesis; Phenols - pharmacology; Physical Sciences; Picrates - chemistry; polyphenolic acid ester; Polyphenols; Science & Technology; Selenium Compounds - chemical synthesis; Selenium Compounds - pharmacology; TRANSFORMATION; CELLS; antioxidant; PHENOLIC ANTIOXIDANTS; PHENOTYPE; polyphenolic acid ester; CAPE; SUPPRESSION; PHENETHYL ESTER; free radical scavenging activity; 5-lipoxygenase inhibition; CAFFEIC ACID; organoselenium compound; GROWTH; DERIVATIVES
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.53.1402

Six novel selenium-containing polyphenolic acid esters were synthesized and evaluated as antioxidants and 5-lipoxygenase inhibitors. Synthesis of the title compounds involved the Mitsunobu reaction of polyphenolic acids (4—8, 14) with 2-phenylselenoethanol (3). Compounds 22, 23, and 25 were found to be very effective antioxidants and 5-lipoxygenase inhibitors with activity comparable to or better than caffeic acid (3,4-dihydroxycinnamic acid) phenethyl ester (CAPE).