|Preferred IUPAC name
|Jmol interactive 3D||Image|
|Molar mass||610.52 g·mol−1|
|Melting point||242 °C (468 °F; 515 K)|
|12.5 mg/100 mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside between the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6))-β-D-glucopyranose). In the fava d'anta tree, the synthesis is done via a rutin synthase activity.
Its name comes from the name of Ruta graveolens, a plant that also contains rutin.
Rutin is a citrus flavonoid glycoside found in many plants including buckwheat, the leaves and petioles of Rheum species, and asparagus. Tartary buckwheat seeds have been found to contain more rutin (about 0.8-1.7% dry weight) than common buckwheat seeds (0.01% dry weight). Rutin is also found in the fruit of the fava d'anta tree (from Brazil), fruits and flowers of the pagoda tree, fruits and fruit rinds (especially the citrus fruits orange, grapefruit, lemon, and lime) and apple; berries such as mulberry, ash tree fruits, aronia berries and cranberries. Rutin is one of the primary flavonols found in 'clingstone' peaches.
Rutin (quercetin rutinoside), like quercitrin, is a glycoside of the flavonoid quercetin. As such, the chemical structures of both are very similar, with the difference existing in the hydroxyl functional group. Both quercetin and rutin are used in many countries as medications for blood vessel protection, and are ingredients of numerous multivitamin preparations and herbal remedies.
Role as ligand
It can combine with cations,[which?] supplying nutrients from the soil to the cells in plants. 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.
Furthermore, it has been shown to inhibit in vitro the vascular endothelial growth factor in subtoxic concentrations, so acts as an inhibitor of angiogenesis. This finding may have potential relevance for the control of some cancers.
While a body of evidence for the effects of rutin and quercetin is available in mice, rats, hamsters, and rabbits, as well as in vitro studies, no clinical studies directly demonstrate significant, positive effects of rutin as dietary supplement in humans.
- Rutin inhibits platelet aggregation, as well as decreases capillary permeability, making the blood thinner and improving circulation.
- Rutin shows anti-inflammatory activity in some animal and in vitro models.
- Rutin inhibits aldose reductase activity. Aldose reductase is an enzyme normally present in the eye and elsewhere in the body. It helps change glucose into the sugar alcohol sorbitol.
- Recent studies show rutin could help prevent blood clots, so could be used to treat patients at risk of heart attacks and strokes.
- Some evidence also shows rutin can be used to treat hemorrhoids, varicosis, and microangiopathy.
- Relatively high amount of rutin increases thyroid iodide uptake in rats and decreases serum T3 and T4 level. The decreased hormone level can be explained by its inhibitory effect produced on Thyroid peroxidase enzyme (TPO).
- Rutin is also an antioxidant; compared to quercetin, acacetin, morin, hispidulin, hesperidin, and naringin, it was found to be the strongest.[unreliable source?] However, in other trials, the effects of rutin were lower or negligible compared to those of quercetin.
Hydroxyethylrutosides, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency.
In veterinary medicine
- Merck Index, 12th Edition, 8456
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- Curbing Clots, Sept, 2012
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- Reporter, Daily Mail (9 May 2012). "Chemical found in apples, onions and green tea can help beat blood clots". London: Mail Online. Retrieved 11 May 2012.
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- quercitrinase on www.brenda-enzymes.org
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