Rutin

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Rutin
Rutin structure.png
Names
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
Preferred IUPAC name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]-4H-chromen-4-one
Other names
Rutoside
Phytomelin
Sophorin
Birutan
Eldrin
Birutan Forte
Rutin trihydrate
Globularicitrin
Violaquercitrin
Identifiers
3D model (JSmol)
ChemSpider
DrugBank
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KEGG
UNII
Properties
C27H30O16
Molar mass 610.52 g·mol−1
Hazards
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]Associate Editor(s)-in-Chief: Sheng Shi, M.D. [2]

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.[3]

Occurrences

Rutin is one of the phenolic compounds found in the invasive plant species Carpobrotus edulis and contributes to the antibacterial[4] and antioxidant[5] properties of the plant.

Its name comes from the name of Ruta graveolens, a plant that also contains rutin.

In food

Rutin is a citrus flavonoid glycoside found in many plants including buckwheat,[6] 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).[6] 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.[7]

Rutin is one of the primary flavonols found in 'clingstone' peaches.[8]

Chemical relatives

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,Template: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[9] in subtoxic concentrations, so acts as an inhibitor of angiogenesis. This finding may have potential relevance for the control of some cancers.

Health effects

While a body of evidence for the effects of rutin and quercetin is available in mice,[10] rats,[11] hamsters,[12] and rabbits,[13] as well as in vitro studies,[14] no clinical studies directly demonstrate significant, positive effects of rutin as dietary supplement in humans.

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

In veterinary medicine

Rutin may have a veterinary use in the management of chylothorax in dogs and cats.[26]

Metabolism

The enzyme quercitrinase can be found in Aspergillus flavus.[27] It is an enzyme in the rutin catabolic pathway.[28]

References

  1. ↑ Merck Index, 12th Edition, 8456
  2. ↑ Krewson, C. F.; Naghski, J. (2006). "Some physical properties of rutin". Journal of the American Pharmaceutical Association. 41 (11): 582–7. doi:10.1002/jps.3030411106. PMID 12999623.
  3. ↑ 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.
  4. ↑ Purification and identification of active antibacterial components in Carpobrotusedulis L. Elmarie van der Watt and Johan C Pretorius, Journal of Ethnopharmacology, Volume 76, Issue 1, June 2001, Pages 87–91, doi:10.1016/S0378-8741(01)00197-0
  5. ↑ Antioxidant and Antibacterial Properties of Mesembryanthemum crystallinum and Carpobrotus edulis Extracts. Bouftira Ibtissem, Chedly Abdelly and Souad Sfar, Advances in Chemical Engineering and Science, 2012, Vol. 2 No. 3, pages 359-365, doi:10.4236/aces.2012.23042
  6. ↑ 6.0 6.1 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.
  7. ↑ Curbing Clots, Sept, 2012
  8. ↑ Chang, S; Tan, C; Frankel, EN; Barrett, DM (2000). "Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars". Journal of agricultural and food chemistry. 48 (2): 147–51. doi:10.1021/jf9904564. PMID 10691607.
  9. ↑ Luo; King, Sarah M.; Chen, Yi Charlie; et al. (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.
  10. ↑ Enkhmaa; Katsube, T; Kitajima, K; Anuurad, E; Yamasaki, M; Yamane, Y; et al. (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.
  11. ↑ Santos; Nagem, TJ; Pinto, AS; Oliveira, MG; et al. (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.
  12. ↑ Auger; Gérain, Peggy; Lequeux, Nadine; Bornet, Aurélie; Serisier, Samuel; Besançon, Pierre; Caporiccio, Bertrand; Cristol, Jean-Paul; 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. |first10= missing |last10= in Authors list (help)
  13. ↑ Juźwiak; Mokrzycki, K; Marchlewicz, M; Białecka, M; Wenda-Rózewicka, L; Gawrońska-Szklarz, B; Droździk, M; et al. (2005). "Effect of quercetin on experimental hyperlipidemia and atherosclerosis in rabbits". Pharmacol Rep. 57 (5): 604–9. PMID 16227643.
  14. ↑ Shen; Lin, HY; Huang, HC; Ko, CH; Yang, LL; Chen, YC; et al. (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.
  15. ↑ Navarro-Núñez; Palomo, M.; Martínez, C.; Vicente, V.; Castillo, J.; Benavente-García, O.; Diaz-Ricart, M.; Escolar, G.; 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. |first10= missing |last10= in Authors list (help)
  16. ↑ Guardia; Juarez, AO; Pelzer, LE; et al. (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.
  17. ↑ Chan Hun Jung; Cho, Chul Hyung; Kim, Chang Jong; et al. (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.
  18. ↑ G. Bhanuprakash Reddy1,*, P. Muthenna1, C. Akileshwari1, Megha Saraswat1 and J. Mark Petrash2. "Inhibition of aldose reductase and sorbitol accumulation by dietary rutin". Current Science. 101 (9): 1191–1197.
  19. ↑ 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.
  20. ↑ http://www.naturalstandard.com/index-abstract.asp?create-abstract=/monographs/herbssupplements/patient-rutin.asp
  21. ↑ http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0073908
  22. ↑ Metodiewa, Diana; Kochman, Agata; Karolczak, Stefan (1997). "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. 41 (5): 1067. doi:10.1080/15216549700202141.
  23. ↑ http://www.diet-and-health.net/Supplements/Rutin.html
  24. ↑ Bando, Noriko; Muraki, Naomi; Murota, Kaeko; Terao, Junji; Yamanishi, Rintaro (2010). "Ingested quercetin but not rutin increases accumulation of hepatic β-carotene in BALB/c mice". Molecular Nutrition & Food Research. 54: S261. doi:10.1002/mnfr.200900329.
  25. ↑ Chow, Jyh-Ming; Shen, Shing-Chuan; Huan, Steven K.; Lin, Hui-Yi; Chen, Yen-Chou (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.
  26. ↑ PMID 16187718 (PMID 16187718)
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  27. ↑ quercitrinase on www.brenda-enzymes.org
  28. ↑ Tranchimand, Sylvain; Brouant, Pierre; Iacazio, Gilles (2010). "The rutin catabolic pathway with special emphasis on quercetinase". Biodegradation. 21 (6): 833–59. doi:10.1007/s10532-010-9359-7. PMID 20419500.

Template:Flavonol Template:Vasoprotectives

Template:Chembox header| Rutin
Rutin
Systematic name 2-(3,4-dihydroxyphenyl)-
4,5-dihydroxy-3-[3,4,5-
trihydroxy-6-[(3,4,5-
trihydroxy-6-methyl-
oxan-2-yl)oxymethyl]
oxan-2-yl]oxy-chromen-
7-one
Chemical formula C27H30O16
Molecular mass 610.52 g/mol
Density x.xxx g/cm3
Melting point xx.x °C
Boiling point xx.x °C
CAS number [153-18-4]
SMILES xxxxx
Template:Chembox header | Disclaimer and references

Rutin, also called rutoside, quercetin-3-rutinoside and sophorin, is a citrus flavonoid glycoside found in buckwheat, the leaves and petioles of Rheum species, and the fruit of the Fava D'Anta tree (from Brazil), as well as other sources. Rutin is the glycoside between the flavonol quercetin and the disaccharide rutinose.

It can combine with cations, 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, and therefore plays a role in inhibiting some cancers.

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.



External links

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