|Preferred IUPAC name
|Jmol 3D model||Interactive 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). It is a citrus flavonoid found in a wide variety of plants including citrus fruit.
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, 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,[medical citation needed] 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.
The cannabinoid mediated antidepressant activity of rutin shown in mice models employing weight-loaded forced swim test. Rutin treatment showed upregulation of CB1 receptors in mouse brain tissue demonstrating antifatigue activity and CB1 receptor-interacting proteins. Further, in brain tissues, an increase in expression of peroxisome proliferator-activated receptor-α coactivator (PGC-1α) and sirtuin 1 (SIRT1) was also demonstrated. Integrating together the cannabinoid, PPAR-γ, and opioid receptor activities, rutin may be a potential multitargeted polypharmacological agent in prevention and treatment of diseases involving dysregulation of PPAR and ECS.
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.
- Rutin produces antinociceptive effects involving central modulation of the vlPAG descending circuit partly mediated by an opioidergic mechanism 
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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- Sharma, Charu; Sadek, Bassem; Goyal, Sameer N.; Sinha, Satyesh; Kamal, Mohammad Amjad; Ojha, Shreesh (2015-01-01). "Small Molecules from Nature Targeting G-Protein Coupled Cannabinoid Receptors: Potential Leads for Drug Discovery and Development". Evidence-based Complementary and Alternative Medicine : eCAM. 2015. doi:10.1155/2015/238482. ISSN 1741-427X. PMC . PMID 26664449.
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- Juźwiak S, Wójcicki J, Mokrzycki K, Marchlewicz M, Białecka M, Wenda-Rózewicka L, Gawrońska-Szklarz B, Droździk M (2005). "Effect of quercetin on experimental hyperlipidemia and atherosclerosis in rabbits". Pharmacological Reports. 57 (5): 604–9. PMID 16227643.
- Shen SC, Lee WR, Lin HY, Huang HC, Ko CH, Yang LL, Chen YC (Jun 2002). "In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E(2) production". European Journal of Pharmacology. 446 (1-3): 187–94. doi:10.1016/S0014-2999(02)01792-2. PMID 12098601.
- Navarro-Núñez L, Lozano ML, Palomo M, Martínez C, Vicente V, Castillo J, Benavente-García O, Diaz-Ricart M, Escolar G, Rivera J (May 2008). "Apigenin inhibits platelet adhesion and thrombus formation and synergizes with aspirin in the suppression of the arachidonic acid pathway". Journal of Agricultural and Food Chemistry. 56 (9): 2970–6. doi:10.1021/jf0723209. PMID 18410117.
- Guardia T, Rotelli AE, Juarez AO, Pelzer LE (Sep 2001). "Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat". Farmaco. 56 (9): 683–7. doi:10.1016/S0014-827X(01)01111-9. PMID 11680812.
- Jung CH, Lee JY, Cho CH, Kim CJ (2007). "Anti-asthmatic action of quercetin and rutin in conscious guinea-pigs challenged with aerosolized ovalbumin". Archives of Pharmacal Research. 30 (12): 1599–607. doi:10.1007/BF02977330. PMID 18254248.
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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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- Chen YT, Zheng RL, Jia ZJ, Ju Y. Flavonoids as superoxide scavengers and antioxidants. Free Radic Biol Med 1990;9(1):19-21.
- Bando N, Muraki N, Murota K, Terao J, Yamanishi R (Jul 2010). "Ingested quercetin but not rutin increases accumulation of hepatic beta-carotene in BALB/c mice". Molecular Nutrition & Food Research. 54 Suppl 2: S261–7. doi:10.1002/mnfr.200900329. PMID 20373287.
- Chow JM, Shen SC, Huan SK, Lin HY, Chen YC (Jun 2005). "Quercetin, but not rutin and quercitrin, prevention of H2O2-induced apoptosis via anti-oxidant activity and heme oxygenase 1 gene expression in macrophages". Biochemical Pharmacology. 69 (12): 1839–51. doi:10.1016/j.bcp.2005.03.017. PMID 15876423.
- Hernandez-Leon A, Fernández-Guasti A, González-Trujano ME (2016). "Rutin antinociception involves opioidergic mechanism and descending modulation of ventrolateral periaqueductal grey matter in rats". Eur J Pain. 20: 274–83. doi:10.1002/ejp.720. PMID 25919941.
- Kopko SH (Aug 2005). "The use of rutin in a cat with idiopathic chylothorax". The Canadian Veterinary Journal. La Revue Vétérinaire Canadienne. 46 (8): 729–31. PMC . PMID 16187718.
- quercitrinase on www.brenda-enzymes.org
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