RefDoc
Haut

Faire une nouvelle recherche
Make a new search
Lancer la recherche


Titre du document / Document title

Nα-(1 -Deoxy-D-fructos-1 -yl)-L-histidine ("D-Fructose-L-histidine") : a Potent Copper Chelator from Tomato Powder

Auteur(s) / Author(s)

MOSSINE Valeri V. (1) ; MAWHINNEY Thomas P. (1) ;

Affiliation(s) du ou des auteurs / Author(s) Affiliation(s)

(1) Department of Biochemistry, University of Missouri-Columbia, Agriculture Bldg, Room 4, Columbia, Missouri 65211, ETATS-UNIS

Résumé / Abstract

Dried fruits and vegetables are known for their high content of D-fructose-amino acids, or Amadori compounds, which appear at the initial step of the Maillard reaction and may participate in redox reactions mediated by trace metals. In this study, we investigated complexation between Cu(ll) and Nα-(1 -deoxy-D-fructos-1 -yl)-L-histidine (D-fructose-L-histidine, FruHis). The content of FruHis in two types of commercial tomato powders was estimated by GLC-MS, using single ion monitoring of trimethylsilylated FruHis hydroxyoximate, as 40 mg/100 g, whereas the concentration of free histidine in the powder samples was about 53 mg/100 g. The Cu(ll)-binding ability of FruHis was studied along with structurally related molecules L-histidine, dipeptide L-carnosine, and Nα-(1-deoxy-D-fructos-1-yl)-L-arginine (FruArg) at 25 °C using pH-potentiometric titrations. Analysis of the titration curves showed that formation of Cu(ll)-FruHis complex species occurs at pH values as low as 2 and that the complexes were redox stable in the pH range 2-10.5, at least for the time of the experiment. At physiological pH, Cu(ll) and FruHis form a dominant coordination species of composition MLH_1 (log β = 5.67), with a presumably deprotonated anomeric hydroxyl group of the fructose portion. The apparent stability constant of 1:1 complexes formed by FruHis and Cu(ll) in neutral aqueous solutions is about 104 times higher than similar values calculated for L-histidine, L-carnosine, and FruArg. FruHis nearly completely protected hydroxyl radical-mediated fragmentation of polymeric DNA in the presence of the Cu/H2O2/ascorbate system, whereas neither of the reference compounds could inhibit the DNA fragmentation as efficiently in similar conditions. These results warrant further investigation of FruHis as a potential food-related antioxidant.

Revue / Journal Title

Journal of agricultural and food chemistry    ISSN  0021-8561   CODEN JAFCAU 

Source / Source

2007, vol. 55, no25, pp. 10373-10381 [9 page(s) (article)] (38 ref.)

Langue / Language

Anglais

Editeur / Publisher

American Chemical Society, Washington, DC, ETATS-UNIS  (1953) (Revue)

Mots-clés anglais / English Keywords

Vegetables

;

Heavy metal

;

Inorganic element

;

Aminoacid

;

Chelation

;

Antioxidant

;

Arginine

;

Powder

;

Tomato

;

Chelating agent

;

Copper

;

Fructose

;

Histidine

;

Mots-clés français / French Keywords

Légume

;

Métal lourd

;

Elément minéral

;

Aminoacide

;

Chélation

;

Antioxydant

;

Arginine

;

Poudre

;

Tomate

;

Chélateur

;

Cuivre

;

Fructose

;

Histidine

;

Mots-clés espagnols / Spanish Keywords

Hortalizas

;

Metal pesado

;

Elemento inorgánico

;

Aminoácido

;

Quelación

;

Antioxidante

;

Arginina

;

Polvo

;

Tomate

;

Quelante

;

Cobre

;

Fructosa

;

Histidina

;

Mots-clés d'auteur / Author Keywords

Amadori compound

;

D-fructose-L-histidine

;

Nα-(1-deoxy-D-fructos-1-yl)-L-histidine

;

d-fructose- L-arginine

;

Nα-(1-deoxy-D-fructos-1-yl)-L-arginine

;

histidine

;

carnosine

;

tomato

;

antioxidant

;

copper

;

chelation

;

GLC-MS

;

Localisation / Location

INIST-CNRS, Cote INIST : 7332, 35400017430639.0420

Nº notice refdoc (ud4) : 19901795



Faire une nouvelle recherche
Make a new search
Lancer la recherche
Bas