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Complexes of iron with phenolic compounds from soybean nodules and other legume tissues: prooxidant and antioxidant properties

AuthorsMorán, José F. ; Klucas, R. V.; Grayer, Renée J.; Abián, Joaquín ; Becana Ausejo, Manuel
Free radicals
Iron chelates
Legume nodules
Oxidant damage
Oxidative stress
Plant phenolics
Issue Date1997
CitationFree Radical Biology and Medicine 22 (5): 861–870 (1997)
AbstractThe low-molecular-mass fraction of the soybean nodule cytosol contains Fe capable of catalyzing free radical production through Fenton chemistry. A large portion of the pool of catalytic Fe, measured as bleomycin-detectable Fe, was characterized as complexes of Fe with phenolic compounds of three classes: phenolic acids, cinnamic acids, and flavonoids. Many of these compounds, along with other phenolics present in legume tissues, were used for a systematic structure–activity relationship study. All phenolics tested were able to chelate Fe, as judged from their inhibitory effect on site-specific deoxyribose degradation (minus EDTA assay). However, only those having catechol, pyrogallol, or 3-hydroxy-4-carbonyl groupings were potent chelators and reductants of Fe3+ at pH 5.5. The same phenolics promoted oxidative damage to DNA (bleomycin assay) and to deoxyribose (plus EDTA assay), but inhibited linolenic acid peroxidation by chelating and reducing Fe3+ and by neutralizing lipid radicals. Also, phenolics having a pyrogallol nucleus attenuated the free radical-mediated inactivation of glutamine synthetase, which was used as a model system, by chelating Fe2+. It is reasoned that under the microaerobic (10–20 nM O2) and acidic (pH 5.5–6.4) conditions prevailing in nodules, phenolics are likely to act primarily as antioxidants, decreasing oxidative damage to biomolecules.
Description24 Pags. The definitive version, with Figs. and Tabls., is available at: http://www.sciencedirect.com/science/journal/08915849
Publisher version (URL)http://dx.doi.org/10.1016/S0891-5849(96)00426-1
Appears in Collections:(EEAD) Artículos
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