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
Quercetin rutinoside
Identifiers
153-18-4 YesY
3D model (Jmol) Interactive image
ChemSpider 4444362 N
DrugBank DB01698 YesY
ECHA InfoCard 100.005.287
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
C05CA01 (WHO)
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). It is a citrus flavonoid found in a wide variety of plants including citrus fruit.

Occurrences

Rutin is one of the phenolic compounds found in the invasive plant species Carpobrotus edulis and contributes to the antibacterial[3] 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,[4] 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).[4] 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.[5] Rutin is one of the primary flavonols found in 'clingstone' peaches.[6] It is also found in green tea infusions.[7]

Approximate rutin content per 100g of selected foods, based on the Phenol-Explorer database:[8]

332 mg Capers, spice
45 mg Olive [Black], raw
36 mg Buckwheat, whole grain flour
23 mg Asparagus, raw
19 mg Black raspberry, raw
11 mg Red raspberry, raw
9 mg Buckwheat, groats, thermally treated
6 mg Buckwheat, refined flour
6 mg Greencurrant
6 mg Plum, fresh
5 mg Blackcurrant, raw
4 mg Blackberry, raw
3 mg Tomato [Cherry], whole, raw
2 mg prune
2 mg Fenugreek, fresh
2 mg Marjoram, dried
2 mg Tea [Black], infusion
1 mg Grape, raisin
1 mg Zucchini, raw
1 mg Apricot, raw
1 mg Tea [Green], infusion
0 mg apple
0 mg redcurrant
0 mg Grape [Green]
0 mg Tomato, whole, raw

Chemical relatives

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, 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[9] 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.[10]

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.[29]

Metabolism

The enzyme quercitrinase can be found in Aspergillus flavus.[30] It is an enzyme in the rutin catabolic pathway.[31]

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. ↑ van der Watt E, Pretorius JC (2001). "Purification and identification of active antibacterial components in Carpobrotusedulis L.". Journal of Ethnopharmacology. 76 (1): 87–91. doi:10.1016/S0378-8741(01)00197-0. PMID 11378287.
  4. 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.
  5. ↑ Curbing Clots, Sept, 2012
  6. ↑ 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.
  7. ↑ Malagutti AR, Zuin V, Cavalheiro É, Henrique Mazo L (2006). "Determination of Rutin in Green Tea Infusions Using Square‐Wave Voltammetry with a Rigid Carbon‐Polyurethane Composite Electrode". Electroanalysis. 18 (10): 1028–1034. doi:10.1002/elan.200603496.
  8. ↑ foods in which the polyphenol Quercetin 3-O-rutinoside is found
  9. ↑ 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.
  10. ↑ 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 4664820Freely accessible. PMID 26664449.
  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. ↑ Chen YT, Zheng RL, Jia ZJ, Ju Y. Flavonoids as superoxide scavengers and antioxidants. Free Radic Biol Med 1990;9(1):19-21.
  26. ↑ 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.
  27. ↑ 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.
  28. ↑ 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.
  29. ↑ 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 1180424Freely accessible. PMID 16187718.
  30. ↑ quercitrinase on www.brenda-enzymes.org
  31. ↑ 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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