Vicine is an

alkaloid Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar ...

glycoside In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycoside ...

found mainly in

fava bean ''Vicia faba'', commonly known as the broad bean, fava bean, or faba bean, is a species of vetch, a flowering plant in the pea and bean family Fabaceae. It is widely cultivated as a crop for human consumption, and also as a cover crop. Var ...

s, which are also called broad beans (''

Vicia faba ''Vicia faba'', commonly known as the broad bean, fava bean, or faba bean, is a species of vetch, a flowering plant in the pea and bean family Fabaceae. It is widely cultivated as a crop for human consumption, and also as a cover crop. Varieti ...

)''. Vicine is toxic in individuals who have a hereditary loss of the enzyme glucose-6-phosphate dehydrogenase. It causes

haemolytic anaemia Hemolytic anemia or haemolytic anaemia is a form of anemia due to hemolysis, the abnormal breakdown of red blood cells (RBCs), either in the blood vessels (intravascular hemolysis) or elsewhere in the human body (extravascular). This most commonly ...

, called favism. The formation of vicine in ''Vicia faba'' has been studied, but this natural formation has not yet been found.

History

Vicine was initially isolated in 1870 from the seeds of ''Vicia sativa'' by a method of extraction with sulfuric acid and subsequent

precipitation In meteorology, precipitation is any product of the condensation of atmospheric water vapor that falls under gravitational pull from clouds. The main forms of precipitation include drizzle, rain, sleet, snow, ice pellets, graupel and hail. ...

with mercury sulfate (HgSO₄). Later vicine was also found in other Vicia species, namely ''Vicia faba'', beet juice and peas. The chemical structure of the compound was built gradually. First the glycosidic nature of the compound was recognized in 1896. The same year the

aglycone An aglycone (aglycon or genin) is the compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid molecule. Detection A way to identify aglycone ...

of vicine, divicine, was isolated. In the beginning of the 20th century the pyrimidine structure was recognized. Despite these initial successes, the correct formula of vicine was determined only in 1953 and it is 2,4-diamino-6-oxypyrimidine-5-(ß-d-glucopyranoside).

Metabolism

Vicine is an inactive compound in the body. When vicine enters the body through food, it is hydrolysed by the intestinal microflora to a highly reactive

free radical A daughter category of ''Ageing'', this category deals only with the biological aspects of ageing. Ageing Ailments of unknown cause Biogerontology Biological processes Causes of death Cellular processes Gerontology Life extension Metabo ...

generating compound, the aglycone divicine. Upon

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution, elimination, and solvation reactions in which water is the nucleophile. Biological hydrolys ...

, the glucose part of the molecule is split off and that results in the reduced divicine. Divicine is then taken up in the blood through the

intestinal epithelium The intestinal epithelium is the single cell layer that form the Lumen (anatomy), luminal surface (lining) of both the Small intestine, small and large intestine (colon) of the Human gastrointestinal tract, gastrointestinal tract. Composed of ...

Adverse effects

Adverse effects almost solely occur in humans that suffer from

glucose-6-phosphate dehydrogenase deficiency Glucose-6-phosphate dehydrogenase deficiency (G6PDD), which is the most common enzyme deficiency worldwide, is an inborn error of metabolism that predisposes to red blood cell breakdown. Most of the time, those who are affected have no symptoms. ...

. This deficiency causes a shortage of

glutathione Glutathione (GSH, ) is an antioxidant in plants, animals, fungi, and some bacteria and archaea. Glutathione is capable of preventing damage to important cellular components caused by sources such as reactive oxygen species, free radicals, pe ...

erythrocytes Red blood cells (RBCs), also referred to as red cells, red blood corpuscles (in humans or other animals not having nucleus in red blood cells), haematids, erythroid cells or erythrocytes (from Greek ''erythros'' for "red" and ''kytos'' for "holl ...

and glutathione is needed for the neutralization of ROS (

reactive oxygen species In chemistry, reactive oxygen species (ROS) are highly reactive chemicals formed from diatomic oxygen (). Examples of ROS include peroxides, superoxide, hydroxyl radical, singlet oxygen, and alpha-oxygen. The reduction of molecular oxygen () p ...

) created by the strongly

reducing agent In chemistry, a reducing agent (also known as a reductant, reducer, or electron donor) is a chemical species that "donates" an electron to an (called the , , , or ). Examples of substances that are commonly reducing agents include the Earth me ...

divicine.

Indications

Persons with G6PD deficiency are asymptomatic. An attack of acute haemolytic anaemia can appear out of nowhere and can be very severe and life-threatening. Indications of such a sudden attack of favism are dark urine, pallor, jaundice, abdominal pain and in most cases fever.

Toxicity

The β-glycosidic bond between glucose and the hydroxyl group at C5 on the pyrimidine ring are hydrolysed to yield the

of vicine, divicine (2,6-diamino-4,5-dihydroxypyrimidine). These aglycones have a strong oxidising capacity for

. In healthy individuals, this is not a problem, as glutathione can be reduced quickly enough to regenerate it. In individuals with a deficiency for

glucose 6-phosphate dehydrogenase Glucose-6-phosphate dehydrogenase (G6PD or G6PDH) () is a cytosolic enzyme that catalyzes the chemical reaction : D-glucose 6-phosphate + NADP+ + H2O 6-phospho-D-glucono-1,5-lactone + NADPH + H+ This enzyme participates in the pentose phosp ...

(G6PD) however, this results in

Effects on animals

A 10 g vicine /kg diet in laying hens led to reduced feed intake, egg weight, haemoglobin levels and fertility and increased liver weights, liver glutathione levels and plasma lipid levels. A diet with comparable levels of vicine per kg in pigs showed only small effects on protein and energy digestibility. In another study, laying and broiler hens were fed grains that were soaked for different periods of time, which partly or totally removed vicine. Hens that had had grains with vicine still in them showed a significant decrease in corpuscular haemoglobin, while the others did not. An in vivo study in rats showed that oral administration of vicine resulted in only small reductions in glutathione concentrations and no mortality.

Intraperitoneal The peritoneum is the serous membrane forming the lining of the abdominal cavity or coelom in amniotes and some invertebrates, such as annelids. It covers most of the intra-abdominal (or coelomic) organs, and is composed of a layer of mesothel ...

administration however, led to a rapid decrease in glutathione followed by death because of anoxia.

References

External links

*
Cornell U. page on vicine
{{Glycosides Alkaloid glycosides Pyrimidones Alkaloids found in Fabaceae Plant toxins