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Chemical Compound Review:

Isouramil 6-amino-5-hydroxy-1H- pyrimidine-2,4-dione

Synonyms: AG-K-61522, SureCN2236804, SureCN3167524, SureCN3167526, SureCN4294778, ...

Naber, E.C. et al., Arese, P. et al., Aruoma, O.I. et al., Morelli, A. et al., Arese, P. et al., et al.

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Disease relevance of Isouramil

Incubation of GSH depleted human erythrocytes with divicine and isouramil did not induce lipid peroxidation and hemolysis in spite of a substantial release of iron [1].
It is possible that the hydrolysis product of vicine, divicine or the analogous product from convicine, isouramil, or both, may be involved in toxicity, because these substances are known to be the cause of a hemolytic anemia in some humans that suffer from favism due to consumption of field beans [2].

High impact information on Isouramil

Red blood cells (RBC) from favic patients are characterized by (a) severe oxidative damage (contributed by autoxidation of divicine and isouramil, two pyrimidine aglycones present in fava beans) and (b) greatly increased calcium levels [3].
2,6-Diamino-4-hydroxy-5-formamidopyrimidine, 5,6-dihydroxycytosine, 4,6-diamino-5-formamidopyrimidine, and 8-hydroxyguanine were proposed as the products in DNA to measure if one aims to measure DNA products as indices of oxidative DNA damage involving hydroxyl radicals in vivo [4].
The cytotoxic pyrimidines, dialuric acid, divicine and isouramil, readily release iron from ferritin and promote ferritin-dependent lipid peroxidation [5].
3. Toxic substances of Vicia faba and their mechanism of action: treatment of G6PD-deficient RBC with divicine or isouramil (redox substances present in fava beans) provokes the same changes as observed during favism [6].
Plasmodia within the G6PD deficient erythrocytes were markedly more sensitive to the inhibitory activity of CFF or the oxidizing agents diamide and isouramil [7].

Biological context of Isouramil

Their active aglycones divicine and isouramil have equivalent metabolic effects [8].

Associations of Isouramil with other chemical compounds

Mouse erythrocytes were incubated with oxidizing agents, phenylhydrazine, divicine and isouramil [9].
Isouramil oxidizes NADH at a much lesser extent than NADPH [8].

Gene context of Isouramil

Effect of divicine and isouramil on red cell metabolism in normal and G6PD-deficient (Mediterranean variant) subjects. Possible role in the genesis of favism [8].

References

Protection against oxidative damage of erythrocyte membrane by the flavonoid quercetin and its relation to iron chelating activity. Ferrali, M., Signorini, C., Caciotti, B., Sugherini, L., Ciccoli, L., Giachetti, D., Comporti, M. FEBS Lett. (1997) [Pubmed]
Reproductive performance of hens fed field beans and potential relationships to vicine metabolism. Naber, E.C., Vogt, H., Harnish, S., Krieg, R., Ueberschaer, K.H., Rauch, H.W. Poult. Sci. (1988) [Pubmed]
Favism: impairment of proteolytic systems in red blood cells. Morelli, A., Grasso, M., Meloni, T., Forteleoni, G., Zocchi, E., De Flora, A. Blood (1987) [Pubmed]
Iron ion-dependent modification of bases in DNA by the superoxide radical-generating system hypoxanthine/xanthine oxidase. Aruoma, O.I., Halliwell, B., Dizdaroglu, M. J. Biol. Chem. (1989) [Pubmed]
Ferritin, lipid peroxidation and redox-cycling xenobiotics. Winterbourn, C.C., Vile, G.F., Monteiro, H.P. Free Radic. Res. Commun. (1991) [Pubmed]
Pathophysiology of favism. Arese, P., Mannuzzu, L., Turrini, F. Folia Haematol. Int. Mag. Klin. Morphol. Blutforsch. (1989) [Pubmed]
Inhibition of the intraerythrocytic development of Plasmodium falciparum in glucose-6-phosphate dehydrogenase deficient erythrocytes is enhanced by oxidants and by crisis form factor. Golenser, J., Miller, J., Spira, D.T., Kosower, N.S., Vande Waa, J.A., Jensen, J.B. Trop. Med. Parasitol. (1988) [Pubmed]
Effect of divicine and isouramil on red cell metabolism in normal and G6PD-deficient (Mediterranean variant) subjects. Possible role in the genesis of favism. Arese, P., Bosia, A., Naitana, A., Gaetani, S., D'Aquino, M., Gaetani, G.F. Prog. Clin. Biol. Res. (1981) [Pubmed]
Iron release and membrane damage in erythrocytes exposed to oxidizing agents, phenylhydrazine, divicine and isouramil. Ferrali, M., Signorini, C., Ciccoli, L., Comporti, M. Biochem. J. (1992) [Pubmed]

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