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The antioxidant capability of a series of isoflavonoid and lignan compounds in both cellular and cell-free systems has been investigated, and related to structure. Nordihydroguaiaretic acid exhibited a potent antioxidant activity in both HepG2 and MDA-MB-468 cells (IC50 5.3 and 1.1 microM respectively), as determined by inhibition of 2',7'-dichlorofluorescin oxidation via t-BOOH, although no inhibition was observed with other compounds tested in this system. All compounds inhibited the formation of 8-oxodeoxyguanosine in DNA exposed to hydroxyl radicals via gamma irradiation or the Fenton reaction. Whilst almost complete inhibition of gamma irradiation-induced damage was achieved (IC50 ranged from 0.2 to 0.8 microM), inhibition was less pronounced with the Fenton system. The ability of all compounds to interact with DNA (as well as with reactive oxygen and iron) was also demonstrated by scanning UV spectroscopy, suggesting that the compounds may inhibit DNA oxidation at least in part by binding to DNA. Hydroxyl radical-scavenging, iron-chelating and DNA-binding activity of these compounds supports their proposed role as natural cancer-protective agents.

Original publication

DOI

10.1080/10715769900301661

Type

Journal article

Journal

Free Radic Res

Publication Date

08/1999

Volume

31

Pages

149 - 160

Keywords

Antioxidants, Cell Line, DNA, DNA Damage, Estrogens, Non-Steroidal, Flavonoids, Fluoresceins, Gamma Rays, Humans, Hydroxyl Radical, Iron, Isoflavones, Lignans, Masoprocol, Oxidation-Reduction, Phytoestrogens, Plant Preparations, Reactive Oxygen Species, Spectrophotometry, Ultraviolet, tert-Butylhydroperoxide