Rutin

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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 3D model Interactive image
KEGG C05625 N
PubChem 5280805
RTECS number VM2975000
UNII 5G06TVY3R7 YesY
  • InChI=1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-,15+,17-,18+,20+,21-,22+,23+,26+,27-/m0/s1
  • CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O
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
Vapor pressure {{{value}}}
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,[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[citation needed]. It is also an antioxidant[citation needed].

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.

  • Rutin inhibits platelet aggregation,[16] as well as decreases capillary permeability, making the blood thinner and improving circulation.[citation needed]
  • Rutin shows anti-inflammatory activity in some animal and in vitro models.[17][18]
  • Rutin inhibits aldose reductase activity.[19] 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.[20]
  • Some evidence also shows rutin can be used to treat hemorrhoids, varicosis, and microangiopathy.[21]
  • 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).[22]
  • Rutin is also an antioxidant;[23] compared to quercetin, acacetin, morin, hispidulin, hesperidin, and naringin, it was found to be the strongest.[24][unreliable source?] However, in other trials, the effects of rutin were lower or negligible compared to those of quercetin.[25][26]

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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Curbing Clots, Sept, 2012
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  24. ↑ http://www.diet-and-health.net/Supplements/Rutin.html
  25. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  26. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  27. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  28. ↑ quercitrinase on www.brenda-enzymes.org
  29. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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