Pro-oxidant and anti-oxidant activity of monofructose glycine and monofructose histidine [electronic resource].

Includes references.

Amadori products of monofructose glycine and monofructose histidine were prepared and purified on gram scale. Crystals of both compounds were characterized by TLC, elemental analysis, 13CNMR and FAB spectroscopy. The - NH2 group of histidine is the only nitrogen involved in the production of Amadori product, and the imidazole ring is active and might be participating in the antioxidant activity. Monofructose glycine gave pro-oxidant activity while glycine at the same concentration (15 mM) gave an anti-oxidant effect. It is possible that the amino group is important for the anti-oxidant activity. However, monofructose histidine gave an anti-oxidant effect greater than that of citric acid (15 mM) when the diene formation was measured. On the other hand, histidine at the same concentration also gave an anti-oxidant effect, but less so than its Amadori products. It is possible that the incorporation of sugar moiety enhances this effect. The molecular model of monofructose histidine shows its ability to chelate metals other than histidine. The ligating groups which can co-ordinate with metals are the amidazole nitrogen and the two hydroxyl groups at C3, C4 of the sugar moiety.

Summary in Arabic.

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