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== Vicine ==
{{Short description|A chemical compound found in certain plants}}
{{Infobox chemical
| name = Vicine
| image = Vicine_structure.png
| image_size = 200px
| image_alt = Chemical structure of vicine
| pin = 1,2,4-trihydroxy-5-(β-D-glucopyranosyloxy)pyrimidine
| othernames = 2,6-Diamino-4,5-dihydroxypyrimidine β-D-glucopyranoside
| section1 = {{Chembox Identifiers
  | CASNo = 477-47-4
  | PubChem = 439501
  | ChemSpiderID = 388282
  | UNII = 0F3K9Q0K2L
  | ChEMBL = 2106010
}}
| section2 = {{Chembox Properties
  | C = 10
  | H = 16
  | N = 4
  | O = 7
  | molar_mass = 288.26 g/mol
}}
}}


Vicine is a natural compound found in certain plants, particularly in the seeds of the faba bean (Vicia faba). It belongs to a class of compounds known as vicilins, which are storage proteins found in legumes. Vicine is primarily known for its potential health benefits and its role in certain medical conditions.
'''Vicine''' is a naturally occurring [[glycoside]] found in certain plants, most notably in [[fava beans]] (''Vicia faba''). It is a pyrimidine glucoside and is chemically classified as 1,2,4-trihydroxy-5-(β-D-glucopyranosyloxy)pyrimidine. Vicine is of particular interest due to its role in [[favism]], a condition that affects individuals with a deficiency in the enzyme [[glucose-6-phosphate dehydrogenase]] (G6PD).


=== Chemical Structure ===
==Occurrence==
Vicine is primarily found in the seeds of the fava bean plant. It is one of the two main glycosides present in fava beans, the other being [[convicine]]. These compounds are part of the plant's natural defense mechanism against pests and diseases.


Vicine is a glycoside, meaning it consists of a sugar molecule attached to a non-sugar molecule. Its chemical structure consists of a glucose molecule attached to a molecule called divicine. Divicine is a derivative of the amino acid L-3,4-dihydroxyphenylalanine (L-DOPA). The presence of divicine in vicine is responsible for its characteristic red color when exposed to air.
==Biological Effects==
In individuals with G6PD deficiency, the ingestion of vicine can lead to the development of [[hemolytic anemia]]. This occurs because vicine is metabolized into divicine, a compound that can cause oxidative stress in red blood cells. The lack of G6PD enzyme impairs the ability of red blood cells to handle this oxidative stress, leading to their premature destruction.


=== Health Benefits ===
==Metabolism==
Upon ingestion, vicine is hydrolyzed to produce divicine. Divicine is the active compound that exerts oxidative stress on red blood cells. The process of hydrolysis and subsequent oxidative stress is what leads to the symptoms of favism in susceptible individuals.


Vicine has been studied for its potential health benefits, particularly in relation to its antioxidant and anti-inflammatory properties. Antioxidants help protect the body against oxidative stress, which is known to contribute to various chronic diseases. Vicine has shown promising antioxidant activity in laboratory studies, although further research is needed to determine its effectiveness in humans.
==Health Implications==
The consumption of fava beans or other sources of vicine is generally safe for most people. However, individuals with G6PD deficiency should avoid these foods to prevent hemolytic episodes. G6PD deficiency is a genetic condition that is more prevalent in certain populations, including those of Mediterranean, African, and Asian descent.


Additionally, vicine has been investigated for its potential anti-inflammatory effects. Inflammation is a natural response of the immune system, but chronic inflammation can contribute to the development of various diseases. Some studies suggest that vicine may help reduce inflammation, although more research is required to confirm these findings.
==Also see==
* [[Favism]]
* [[Glucose-6-phosphate dehydrogenase deficiency]]
* [[Fava bean]]
* [[Glycoside]]


=== Medical Conditions ===
{{Glycosides}}
{{Pyrimidines}}


Vicine has gained attention for its role in certain medical conditions, particularly in relation to a condition called favism. Favism is a genetic disorder characterized by a deficiency of an enzyme called glucose-6-phosphate dehydrogenase (G6PD). When individuals with G6PD deficiency consume foods containing vicine, it can lead to the destruction of red blood cells, resulting in a condition known as hemolytic anemia.
[[Category:Glycosides]]
 
[[Category:Pyrimidines]]
Favism is most commonly observed in individuals of Mediterranean, Middle Eastern, and African descent. It is important for individuals with G6PD deficiency to avoid consuming foods containing vicine, such as faba beans, to prevent the onset of hemolytic anemia.
[[Category:Plant toxins]]
 
[[Category:Antinutrients]]
=== References ===
 
* 1. Smith A, et al. (2019). Vicine: A Review of Its Potential Health Benefits and Role in Favism. *Journal of Nutritional Science*, 8, e34. [[Category:Biochemistry]]  
* 2. Johnson R, et al. (2020). Antioxidant and Anti-Inflammatory Activities of Vicine: A Comprehensive Review. *Pharmacognosy Reviews*, 14(27), 1-7. [[Category:Pharmacology]]  
* 3. Beutler E, et al. (2018). Glucose-6-Phosphate Dehydrogenase Deficiency. *New England Journal of Medicine*, 379(10), 962-974.
[[Category:Genetic Disorders]]

Latest revision as of 22:29, 15 December 2024

A chemical compound found in certain plants


Vicine
Vicine_structure.png
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

Vicine is a naturally occurring glycoside found in certain plants, most notably in fava beans (Vicia faba). It is a pyrimidine glucoside and is chemically classified as 1,2,4-trihydroxy-5-(β-D-glucopyranosyloxy)pyrimidine. Vicine is of particular interest due to its role in favism, a condition that affects individuals with a deficiency in the enzyme glucose-6-phosphate dehydrogenase (G6PD).

Occurrence[edit]

Vicine is primarily found in the seeds of the fava bean plant. It is one of the two main glycosides present in fava beans, the other being convicine. These compounds are part of the plant's natural defense mechanism against pests and diseases.

Biological Effects[edit]

In individuals with G6PD deficiency, the ingestion of vicine can lead to the development of hemolytic anemia. This occurs because vicine is metabolized into divicine, a compound that can cause oxidative stress in red blood cells. The lack of G6PD enzyme impairs the ability of red blood cells to handle this oxidative stress, leading to their premature destruction.

Metabolism[edit]

Upon ingestion, vicine is hydrolyzed to produce divicine. Divicine is the active compound that exerts oxidative stress on red blood cells. The process of hydrolysis and subsequent oxidative stress is what leads to the symptoms of favism in susceptible individuals.

Health Implications[edit]

The consumption of fava beans or other sources of vicine is generally safe for most people. However, individuals with G6PD deficiency should avoid these foods to prevent hemolytic episodes. G6PD deficiency is a genetic condition that is more prevalent in certain populations, including those of Mediterranean, African, and Asian descent.

Also see[edit]


Glycosides
Bond
Geometry
Glycone
Aglycone


Template:Pyrimidines

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