Divicine

Divicine
Divicine

pyrimidine tautomer
pyrimidinone tautomer
IUPAC name
2,6-diamino-4,5-dihydroxypyrimidine
Other names
2,6-diamino-4,5-pyrimidinediol; 2,6-diamine-5-hydroxy-4(3H)-pyrimidinone; 2,4-diamino-5,6-dihydroxypyrimidine
Identifiers
CAS number 32267-39-3 [1]
PubChem 91606
ChemSpider 2971290 YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C4H6N4O2
Molar mass 142.12 g mol−1
Appearance Brownish needles
Solubility in water Soluble in 10% KOH
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Divicine (2,6-diamino-4,5-dihydroxypyrimidine) is an oxidant and a base with alkaloidal properties found in fava beans and Lathyrus sativus. It is an aglycone of vicine. A common derivative is the diacetate form (2,6-diamino-1,6-dihydro-4,5-pyrimidinedione).[2]

Contents

Occurrence

Divicine is found in fava beans and in the legume Lathyrus sativus, also known as khesari, which is a cheap and robust food source commonly grown in Asia and East Africa.

Synthesis

In plants, reduced divicine is formed from the hydrolysis of the inactive β–glucoside, vicine.[3]

A simplified three-step process for artificial divicine synthesis: (1) The benzyl group of 2-amino-5-benzyloxy-4-hydroxypyrimidine is removed by acid hydrolysis, yielding 2-amino-4,5-dihydroxypyrimidine. (2) This intermediate is then treated with nitrous acid to yield the slightly soluble orange product, 2-amino-6-nitrosopyrimidine-4,5-diol (3) which is then reduced with sodium dithionite to yield divicine.[4]

Toxicity

Divicine has been deemed a hemotoxic component of fava beans and plays a role in the development of favism, a disorder that involves a hemolytic response to the consumption of broad beans due to glucose-6-phosphate dehydrogenase (G6PD or G6PDH) deficiency. This deficiency, an X-linked recessive hereditary disease, is the most common enzyme deficiency worldwide. It is particularly common in those of African, Asian, Mediterranean, and Middle-Eastern descent. Symptoms of favism include hemolysis, prolonged jaundice, kernicterus, and even acute renal failure in extreme cases.[5]

The specific mechanism of divicine’s toxicity is still unknown. It had been established that the β–glucosides vicine and convicine were linked to the precipitation of hemolytic crises in G6PDH-deficient individuals,[6] but in a more recent study of rat erythrocyte toxicity, exposure to 1.5 mM of divicine dramatically reduced survival rates while exposure to 5 mM of vicine did not. These results suggest that divicine is a direct-acting hemolytic agent and likely the direct cause of favism.[7]

Divicine is also present in and at least partially responsible for the poisonous action of Lathyrus sativus - a legume commonly grown in drought- and famine-prone regions of Asia and East Africa as an ‘insurance crop’ for human consumption and livestock feed when other crops fail to grow, despite their known health hazards.[8]

References

  1. ^ http://www.druglead.com/cds/divicine.html
  2. ^ Bendich, C. (1953). Biochim. Biophys. 12: 462. 
  3. ^ Baker, M.; Bosia, A. (1984). "Mechanism of Action of Divicine in a Cell-free System and in Glucose-6-phosphate Dehydrogenase-deficient Red Cells". Toxicol. Pathol. 12: 331–336. 
  4. ^ Chesterfield, J.; et al. (1964). "194. Pyrimidines. Part XIII. Electrophilic substitution at position 6 and a synthesis of divicine (2,4-diamino-5,6-dihydroxypyrimidine)". J. Chem. Soc.: 1001–1005. 
  5. ^ Frank, J. (2005). "Diagnosis and management of G6PD deficiency". Am. Fam. Phys. 72: 1277–1282. 
  6. ^ Doyle, M. Ellin (1995). Food Safety 1995. Marcel Dekker, Inc.. p. 357. ISBN 0-8247-9624-1. 
  7. ^ McMillan, D.; et al. (2001). "Favism: Effect of Divicine on Rat Erythrocyte Sulfhydryl Status, Hexose Monophosphate Shunt Activity, Morphology, and Membrane Skeletal Proteins". Toxicol. Sci. 62: 353–359. doi:10.1093/toxsci/62.2.353. PMID 11452148. 
  8. ^ http://www.biology-online.org/dictionary/Divicine

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  • divicine — A base with alkaloidal properties present in Lathyrus sativus that is responsible, in part at least, for the latter s poisonous action. See lathyrism. * * * di·vi·cine (di viґsin) a toxic pyrimidine aglycone produced by endogenous degradation of… …   Medical dictionary

  • Deficit en glucose-6-phosphate deshydrogenase — Déficit en glucose 6 phosphate déshydrogénase Déficit en glucose 6 phosphate déshydrogénase Autre nom Favisme Référence MIM …   Wikipédia en Français

  • Déficience en G6PDH — Déficit en glucose 6 phosphate déshydrogénase Déficit en glucose 6 phosphate déshydrogénase Autre nom Favisme Référence MIM …   Wikipédia en Français

  • Déficit En Glucose-6-Phosphate Déshydrogénase — Autre nom Favisme Référence MIM …   Wikipédia en Français

  • Déficit en G6-PD — Déficit en glucose 6 phosphate déshydrogénase Déficit en glucose 6 phosphate déshydrogénase Autre nom Favisme Référence MIM …   Wikipédia en Français

  • Déficit en G6PD — Déficit en glucose 6 phosphate déshydrogénase Déficit en glucose 6 phosphate déshydrogénase Autre nom Favisme Référence MIM …   Wikipédia en Français

  • Déficit en glucose-6-phosphate déshydrogénase — Référence MIM 305900 Transmission Récessive liée à l X Chromosome Xq28 Mutation Ponctuelle Diagnostic prénatal …   Wikipédia en Français

  • Déficit en glucose 6 phosphate déshydrogénase — Autre nom Favisme Référence MIM …   Wikipédia en Français

  • Favisme — Déficit en glucose 6 phosphate déshydrogénase Déficit en glucose 6 phosphate déshydrogénase Autre nom Favisme Référence MIM …   Wikipédia en Français

  • vicine — A glucoside occurring in akta, a weed that contaminates Lathyrus sativus, and in the common vetch (Vicia sativa), a plant whose fruit is substituted for red lentils; thought by some to be responsible for the symptoms of lathyrism. [Vicia (genus… …   Medical dictionary

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