Rutin

Rutin
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
153-18-4 YesY
ChemSpider 4444362 N
DrugBank DB01698 YesY
Jmol interactive 3D Image
KEGG C05625 N
PubChem 5280805
RTECS number VM2975000
UNII 5G06TVY3R7 YesY
Properties
C27H30O16
Molar mass 610.52 g·mol−1
Appearance Solid
Melting point 242 °C (468 °F; 515 K)
12.5 mg/100 mL[1]
13 mg/100mL[2]
Pharmacology
ATC code C05CA01
Hazards
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
0
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

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]

It is also found in green tea infusions.[9]

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

Animal research

While a body of evidence for the effects of rutin and quercetin is available in mice,[11] rats,[12] hamsters,[13] and rabbits,[14] as well as in vitro studies,[15] 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.[27]

Metabolism

The enzyme quercitrinase can be found in Aspergillus flavus.[28] It is an enzyme in the rutin catabolic pathway.[29]

References

  1. ↑ Merck Index, 12th Edition, 8456
  2. ↑ Krewson CF, Naghski J (Nov 1952). "Some physical properties of rutin". Journal of the American Pharmaceutical Association. American Pharmaceutical Association 41 (11): 582–7. doi:10.1002/jps.3030411106. PMID 12999623.
  3. ↑ Lucci N, Mazzafera P (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. 1 2 Kreft S, Knapp M, Kreft I (Nov 1999). "Extraction of rutin from buckwheat (Fagopyrum esculentumMoench) seeds and determination by capillary electrophoresis". Journal of Agricultural and Food Chemistry 47 (11): 4649–52. doi:10.1021/jf990186p. PMID 10552865.
  7. ↑ Curbing Clots, Sept, 2012
  8. ↑ Chang S, Tan C, Frankel EN, Barrett DM (Feb 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. ↑ Determination of Rutin in Green Tea Infusions Using Square‐Wave Voltammetry with a Rigid Carbon‐Polyurethane Composite Electrode. Andréa R. Malagutti, Vânia Zuin, Éder T. G. Cavalheiro and Luiz Henrique Mazo, Electroanalysis, April 2006k 18(10), pages 1028-1034, doi:10.1002/elan.200603496
  10. ↑ Luo H, Jiang BH, King SM, Chen YC (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.
  11. ↑ Enkhmaa B, Shiwaku K, Katsube T, Kitajima K, Anuurad E, Yamasaki M, Yamane Y (Apr 2005). "Mulberry (Morus alba L.) leaves and their major flavonol quercetin 3-(6-malonylglucoside) attenuate atherosclerotic lesion development in LDL receptor-deficient mice". The Journal of Nutrition 135 (4): 729–34. PMID 15795425.
  12. ↑ Santos KF, Oliveira TT, Nagem TJ, Pinto AS, Oliveira MG (Dec 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.
  13. ↑ Auger C, Teissedre PL, Gérain P, Lequeux N, Bornet A, Serisier S, Besançon P, Caporiccio B, Cristol JP, Rouanet JM (Mar 2005). "Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation". Journal of Agricultural and Food Chemistry 53 (6): 2015–21. doi:10.1021/jf048177q. PMID 15769129.
  14. ↑ 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.
  15. ↑ 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.
  16. ↑ 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.
  17. ↑ 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.
  18. ↑ 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.
  19. ↑ Reddy GB, Muthenna P, Akileshwari C, Saraswat M, Petrash JM. "Inhibition of aldose reductase and sorbitol accumulation by dietary rutin". Current Science 101 (9): 1191–1197.
  20. ↑ 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.
  21. ↑ http://www.naturalstandard.com/index-abstract.asp?create-abstract=/monographs/herbssupplements/patient-rutin.asp
  22. ↑ http://www.plosone.org/article/info%3Adoi%2F10.1371%2Fjournal.pone.0073908
  23. ↑ Metodiewa D, Kochman A, Karolczak S (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): 1067–1075. doi:10.1080/15216549700202141.
  24. ↑ http://www.diet-and-health.net/Supplements/Rutin.html
  25. ↑ 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.
  26. ↑ 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.
  27. ↑ 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 1180424. PMID 16187718.
  28. ↑ quercitrinase on www.brenda-enzymes.org
  29. ↑ Tranchimand S, Brouant P, Iacazio G (Nov 2010). "The rutin catabolic pathway with special emphasis on quercetinase". Biodegradation 21 (6): 833–59. doi:10.1007/s10532-010-9359-7. PMID 20419500.
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