Rutin
| Rutin | |
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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 |
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2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-4H-chromen-4-one |
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Other names
Rutoside |
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| Identifiers | |
| CAS number | 153-18-4  |
| PubChem | 5280805 |
| ChemSpider | 4444362  |
| UNII | 5G06TVY3R7 |
| DrugBank | DB01698 |
| RTECS number | VM2975000 |
| ATC code | C05 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C27H30O16 |
| Molar mass | 610.517 g/mol |
| Exact mass | 610.153385 u |
| Appearance | solid |
| Melting point |
242 °C, 515 K, 468 °F |
| Solubility in water | insoluble |
| Hazards | |
| NFPA 704 |
 0
2
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 (verify) (what is:  / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Rutin, also called rutoside, quercetin-3-O-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 flowers of the pagoda tree, fruits and fruit rinds (especially citrus fruits (orange, grapefruit, lemon, lime)) and berries such as mulberry, ash tree fruits and cranberries. Its name comes from the name of Ruta graveolens, a plant that also contains rutin. It is sometimes referred to as vitamin P, although not strictly a vitamin.[2]
Rutin is the glycoside between the flavonol quercetin and the disaccharide rutinose (α-L-Rhamnopyranosyl-(1→6))-β-D-glucopyranose). In fava d'anta, the synthesis is done via a rutin synthase activity.[3]
Contents |
[edit] Chemical relatives
Rutin (quercetin rutinoside), as well as 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.[4]
[edit] 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.
Furthermore, it has been shown to inhibit in vitro the vascular endothelial growth factor[5] in subtoxic concentrations, so acts as an inhibitor of angiogenesis. This finding can be potentially relevant for the control of some cancers.
[edit] Health effects
While there is a body of evidence for the effects of rutin and quercetin in mice[6], rats[7], hamsters[8] and rabbits[9], as well as in vitro studies[10], no clinical studies directly demonstrating significant, positive effects of rutin as dietary supplement in humans exist.
- Rutin inhibits platelet aggregation,[11] as well as decreasing capillary permeability, making the blood thinner and improving circulation.[citation needed]
- Rutin shows anti-inflammatory activity in some animal and in vitro models.[12][13]
- Rutin inhibits aldose reductase activity[citation needed]. Aldose reductase is an enzyme normally present in the eye and elsewhere in the body. It helps change glucose into the sugar alcohol sorbitol.
- Rutin also strengthens the capillaries[citation needed], and, therefore, can reduce the symptoms of haemophilia. It also may help to prevent a common, unpleasant-looking, venous edema of the legs; however, a double-blind clinical study on the effect of buckwheat tea containing rutin did not show a significant effect above placebo.[14]
- Rutin, as ferulic acid, can reduce the cytotoxicity of oxidized LDL cholesterol and lower the risk of heart disease.[citation needed]
- There is also some evidence that rutin can be used to treat hemorrhoids, varicosis, and microangiopathy.[4]
- Rutin is also an antioxidant;[15] compared to quercetin, acacetin, morin, hispidulin, hesperidin, and naringin, it was found to be the strongest.[16] However, in other trials, the effects of rutin were lower or negligible compared to those of quercetin.[17][18]
Hydroxyethylrutosides, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency.
[edit] In veterinary medicine
Rutin has a veterinary use in the management of chylothorax in dogs and cats.[19]
[edit] Metabolism
The enzyme quercitrinase can be found in Aspergillus flavus.[20] It is an enzyme in the rutin catabolic pathway.[21]
[edit] References
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This article needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (October 2010) |
- ^ Kreft S, Knapp M, Kreft I (November 1999). "Extraction of rutin from buckwheat (Fagopyrum esculentum Moench) seeds and determination by capillary electrophoresis". J. Agric. Food Chem. 47 (11): 4649–52. doi:10.1021/jf990186p. PMID 10552865.
- ^ http://www.herbalextractsplus.com/rutin.cfm
- ^ Lucci; Mazzafera (2009). "Rutin synthase in fava d'anta: Purification and influence of stressors". Canadian journal of plant science 89 (5): 895–902. doi:10.4141/CJPS09001. http://cat.inist.fr/?aModele=afficheN&cpsidt=21997861.
- ^ a b http://www.naturalstandard.com/index-abstract.asp?create-abstract=/monographs/herbssupplements/patient-rutin.asp
- ^ Luo; et al.; King, Sarah M.; Chen, Yi Charlie (2008). "Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids". Nutrition and Cancer 60 (6): 800–9. doi:10.1080/01635580802100851. PMID 19005980.
- ^ Enkhmaa; et al.; Katsube, T; Kitajima, K; Anuurad, E; Yamasaki, M; Yamane, Y (2005). "Mulberry (Morus alba L.) leaves and their major flavonol quercetin 3-(6-malonylglucoside) attenuate atherosclerotic lesion development in LDL receptor-deficient mice". J Nutr 135 (4): 729–34. PMID 15795425.
- ^ Santos; et al.; Nagem, TJ; Pinto, AS; Oliveira, MG (1999). "HYPOLIPIDAEMIC EFFECTS OF NARINGENIN, RUTIN, NICOTINIC ACID AND THEIR ASSOCIATIONS". Pharmacological Research 40 (6): 493–6. doi:10.1006/phrs.1999.0556. PMID 10660947.
- ^ Auger; et al.; Gérain, Peggy; Lequeux, Nadine; Bornet, Aurélie; Serisier, Samuel; Besançon, Pierre; Caporiccio, Bertrand et al (2005). "Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation". J Agric Food Chem. 53 (6): 2015–21. doi:10.1021/jf048177q. PMID 15769129.
- ^ Juźwiak; et al.; 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". Pharmacol Rep. 57 (5): 604–9. PMID 16227643.
- ^ Shen; et al.; Lin, HY; Huang, HC; Ko, CH; Yang, LL; Chen, YC (2002). "In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E2 production". European Journal of Pharmacology 446 (1–3): 187–94. doi:10.1016/S0014-2999(02)01792-2. PMID 12098601.
- ^ Navarro-Núñez; et al.; Palomo, M.; Martínez, C.; Vicente, V.; Castillo, J.; Benavente-García, O.; Diaz-Ricart, M. et al (2008). "Apigenin Inhibits Platelet Adhesion and Thrombus Formation and Synergizes with Aspirin in the Suppression of the Arachidonic Acid Pathway". J. Agric. Food Chem. 56 (9): 2970–6. doi:10.1021/jf0723209. PMID 18410117.
- ^ Guardia; et al.; Juarez, AO; Pelzer, LE (2001). "Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat". Il Farmaco 56 (9): 683–7. doi:10.1016/S0014-827X(01)01111-9. PMID 11680812.
- ^ Chan Hun Jung; et al.; Cho, Chul Hyung; Kim, Chang Jong (2007). "Anti-asthmatic action of quercetin and rutin in conscious guinea-pigs challenged with aerosolized ovalbumin". Arch. Pharmacal Research 30 (12): 1599–1607. doi:10.1007/BF02977330. http://www.springerlink.com/content/3265v57604507v87.
- ^ Ihme et al. "Leg oedema protection from a buckwheat herb tea in patients with chronic venous insufficiency: a single-centre, randomised, double-blind, placebo-controlled clinical trial", European Journal of Clinical Pharmacology, 50(6):443-447, doi:10.1007/s002280050138
- ^ Metodiewa et al. "Evidence for antiradical and antioxidant properties of four biologically active N,N-Diethylaminoethyl ethers of flavaone oximes: A comparison with natural polyphenolic flavonoid rutin action", IUBMB Life 1997, 41(5):1067–1075, doi:10.1080/15216549700202141
- ^ http://www.diet-and-health.net/Supplements/Rutin.html
- ^ Bando et al. "Ingested quercetin but not rutin increases accumulation of hepatic β-carotene in BALB/c mice" Mol. Nutr. Food Res. 54(S2):S261-7 doi:10.1002/mnfr.200900329
- ^ Chow et al. "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 2005, 69(12):1839-1851, doi:10.1016/j.bcp.2005.03.017
- ^ Kopko, S. H. (2005). "The use of rutin in a cat with idiopathic chylothorax". The Canadian veterinary journal. La revue veterinaire canadienne 46 (8): 729–731. PMC 1180424. PMID 16187718. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1180424.
- ^ quercitrinase on www.brenda-enzymes.org
- ^ The rutin catabolic pathway with special emphasis on quercetinase. Sylvain Tranchimand, Pierre Brouant and Gilles Iacazio, Biodegradation, Volume 21, Number 6, pages 833-859, doi:10.1007/s10532-010-9359-7
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