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Short Paper | Regular issue | Vol 92, No. 1, 2016, pp.120-132
Published online, 8th December, 2015
DOI: 10.3987/COM-15-13363
Antioxidant Effects of the Hydroxy Groups in the Simple Phenolic Carbazoles

Yuhzo Hieda, Noriyuki Hatae, Makoto Anraku, Nobuyasu Matsuura, Kazuhide Uemura, Satoshi Hibino, Tominari Choshi,* Hisao Tomida, Osamu Hori, and Haruto Fujioka*

*Faculty of Pharmacy and Pharmaceutical Sciences, Fukuyama University, Fukuyama, Hiroshima 729-0292, Japan


Antioxidant activities of the simple phenolic carbazoles 5-11 were evaluated by 2,2-diphenyl-1-picrylhydrazyl and 2,2’-azinobis-(3-ethylbenzthiazoline-6-sulfonate)+ radical scavenging assays. The simple phenolic carbazoles 5-7, 9, and 11 exhibited stronger antioxidant activities than α-tocopherol, and similar antioxidant activities as phenolic carbazole alkaloids carazostatin (1), and carbazomadurins A (3) and B (4). Bond dissociation energies and highest occupied molecule orbital energy levels of a series of phenolic carbazoles including phenolic carbazole alkaloids were calculated. The reducing ability of the phenolic carbazole core could be important role for the antioxidant activity of carbazole alkaloids 1, 3, and 4.