Rutin

Rutin
IUPAC name	2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4H-chromen-4-one
Other names	rutoside Phytomelin Sophorin Birutan Eldrin Birutan Forte Rutin trihydrate Globularicitrin Violaquercitrin
Identifiers
CAS number	153-18-4
PubChem	5280805
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5) O)O)O)O)O)O)O)O
Properties
Molecular formula	C27H30O16
Molar mass	610.52 g/mol
Exact mass	610.153385
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Rutin, also called rutoside, quercetin-3-rutinoside and sophorin, is a citrus flavonoid glycoside found in buckwheat,^[1] the leaves and petioles of Rheum species, and asparagus. Rutin is also found in the fruit of the Fava D'Anta tree (from Brazil), fruits and fruit rinds (especially citrus fruits (orange, grapefruit, lemon, lime)) and berries such as mulberry and cranberries. Its name comes from the name of Ruta graveolens, a plant that also contains rutin.

Rutin is the glycoside between the flavonol quercetin and the disaccharide rutinose.

Chemical relatives

Quercetin is a flavonoid with a wide range of biological activities. It mainly occurs in plants as glycosides, such as rutin (quercetin rutinoside) in tea. Quercetin and rutin are used in many countries as medications for blood vessel protection and are ingredients of numerous multivitamin preparations and herbal remedies^{[citation needed]}. Rutin is also called rutoside.

Role as ligand

It can combine with cations^[which?], supplying nutrients from the soil to the cells in plants^{[citation needed]}. In humans, it attaches to the iron ion Fe²⁺, preventing it from binding to hydrogen peroxide, which would otherwise create a highly-reactive free-radical that may damage cells. It is also an antioxidant, and potent VEGF inhibitor (angiogenesis inhibitor) therefore plays a role in inhibiting some cancers.

Health effects

• Rutin inhibits platelet aggregation, making the blood thinner and improves circulation.
• Rutin has anti-inflammatory activity^[2].
• Rutin inhibits aldose reductase activity. Aldose reductase is an enzyme normally present in the eye and elsewhere in the body. It helps change glucose (sugar - glucose) into a sugar alcohol called sorbitol.

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Too much sorbitol trapped in eye and nerve cells can damage these cells, leading to retinopathy and neuropathy. Substances that prevent or slow the action of aldose reductase are being studied as a way to prevent or delay these complications of diabetes. Aldose reductase is the first enzyme in the sorbitol pathway. This pathway is responsible for the conversion of glucose to sorbitol, and of galactose to galactitol. Under conditions of hyperglycemia, sorbitol accumulation occurs. Aldose reductase inhibitors prevent the accumulation of intracellular sorbitol. Whether rutin can help reduce the rate of glaucoma is not clear.

Rutin also strengthens the capillaries, and, therefore, can reduce the symptoms of haemophilia. It also may help to prevent a common unpleasant-looking venous edema of the legs. Rutin, as ferulic acid, can reduce the cytotoxicity of oxidized LDL cholesterol and lower the risk of heart disease.

Hydroxyethylrutosides, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency.

In veterinary medicine

Rutin has a veterinary use in the management of chylothorax in dogs and cats^[3].

References

This article includes a list of references, related reading or external links, but its sources remain unclear because it lacks inline citations. Please improve this article by introducing more precise citations where appropriate. (June 2009)