Journal
FOOD RESEARCH INTERNATIONAL
Volume 38, Issue 4, Pages 395-402Publisher
ELSEVIER
DOI: 10.1016/j.foodres.2004.10.009
Keywords
antiradical activity; caffeic acid; L-cysteine; polyphenol oxidation; reducing power; sodium periodate
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Caffeic acid (3,4-dihydroxycinnamic acid) was oxidized in wine-like model solutions (citrate buffer, pH 3.5) containing L-cysteine, by means of sodium periodate that mimics the mechanism of polyphenol oxidase (PPO). The reaction lead to the formation of a L-cysteine/caffeic acid adduct, which was isolated and tentatively identified as 2-S-cysteinylcaffeic acid (2-CCA), on the basis of LC-MS and H-1 NMR data. The antioxidant properties of 2-CCA were assessed by employing the DPPH and a ferric-reducing test, and compared with both caffeic acid and L-cysteine, but also with gallic acid, which was used as a reference antioxidant. The results indicated that the adduct exhibits slightly improved antiradical activity in relation with the parent molecule (caffeic acid), but its reducing capacity was dramatically reduced, a fact that was theoretically ascribed to its strong chelating ability. (c) 2004 Elsevier Ltd. All rights reserved.
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