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Paper | Regular issue | Vol 92, No. 1, 2016, pp.86-101
Published online, 16th December, 2015
DOI: 10.3987/COM-15-13366
Radical Scavenging Activity of Ascorbic Acid Analogs Containing a Carbonyl Conjugated Ene-Diol Structure

Shogo Nomura, Keiko Inami, and Masataka Mochizuki*

*Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda-shi, Chiba 278-8510, Japan

Abstract

Small molecule antioxidants such as ascorbic acid (AscH2) prevent the oxidative damage of biological molecules by scavenging reactive oxygen species. A carbonyl-conjugated ene-diol structure is essential for the antioxidant activity of AscH2. As such, we synthesized novel AscH2 analogs containing a carbonyl conjugated ene-diol structure and evaluated their radical scavenging activities. When the 1,2-dihydroxyethyl group was removed, radical scavenging activity equal to AscH2 was observed. Analogs containing an endocyclic nitrogen atom instead of a ring oxygen displayed higher radical scavenging activities than AscH2. Therefore, the electron donating effect of the carbonyl conjugated ene-diol structure greatly increased the radical scavenging activity of AscH2 analogs.