Rutin: Difference between revisions
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| Verifiedfields = changed |
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| verifiedrevid = 447706318 |
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| Name = Rutin |
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| verifiedrevid = 455039901 |
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| ImageFile = Rutin structure.svg |
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| Name = Rutin |
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| ImageFile = Rutin structure.svg |
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| ImageSize = 250px |
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| PIN = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[α-<small>L</small>-rhamnopyranosyl-(1→6)-β-<small>D</small>-glucopyranosyloxy]-4''H''-chromen-4-one |
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| ImageName = Rutin |
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| IUPACName = 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,5-trihydroxy-6-({[(2''R'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-4''H''-chromen-4-one |
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| ImageName2 = Rutin 3D |
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| OtherNames=rutoside<br>Phytomelin<br>Sophorin<br>Birutan<br>Eldrin<br>Birutan Forte<br>Rutin trihydrate<br>Globularicitrin<br>Violaquercitrin |
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| IUPACName = 3′,4′,5,7-Tetrahydroxy-3-[α-<small>L</small>-rhamnopyranosyl-(1→6)-β-<small>D</small>-glucopyranosyloxy]flavone |
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| Section1 = {{Chembox Identifiers |
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| SystematicName = (4<sup>2</sup>''S'',4<sup>3</sup>''R'',4<sup>4</sup>''S'',4<sup>5</sup>''S'',4<sup>6</sup>''R'',7<sup>2</sup>''R'',7<sup>3</sup>''R'',7<sup>4</sup>''R'',7<sup>5</sup>''R'',7<sup>6</sup>''S'')-1<sup>3</sup>,1<sup>4</sup>,2<sup>5</sup>,2<sup>7</sup>,4<sup>3</sup>,4<sup>4</sup>,4<sup>5</sup>,7<sup>3</sup>,7<sup>4</sup>,7<sup>5</sup>-Decahydroxy-7<sup>6</sup>-methyl-2<sup>4</sup>''H''-3,6-dioxa-2(2,3)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphane-2<sup>4</sup>-one |
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| CASNo = 153-18-4 |
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| OtherNames=Rutoside <small>([[International nonproprietary name|INN]])</small><br />Phytomelin<br />Sophorin<br />Birutan<br />Eldrin<br />Birutan Forte<br />Rutin trihydrate<br />Globularicitrin<br />Violaquercitrin<br />Quercetin rutinoside |
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| PubChem = 5280805 |
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|Section1={{Chembox Identifiers |
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| RTECS = VM2975000 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 153-18-4 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID = 4444362 |
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| UNII = 5G06TVY3R7 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| SMILES = 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 |
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| KEGG = C05625 |
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| PubChem = 5280805 |
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| RTECS = VM2975000 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01698 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 5G06TVY3R7 |
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| SMILES = 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 |
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| 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 |
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|Section2={{Chembox Properties |
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| C=27 | H=30 | O=16 |
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| Formula = C<sub>27</sub>H<sub>30</sub>O<sub>16</sub> |
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| Appearance = Solid |
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| MolarMass = 610.517 g/mol |
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| Density = |
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| ExactMass = 610.153385 |
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| MeltingPtC = 242 |
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| BoilingPtC = |
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| Solubility = 12.5 mg/100 mL<ref>''[[Merck Index]]'', 12th Edition, '''8456'''</ref><br />13 mg/100mL<ref>{{cite journal | vauthors = Krewson CF, Naghski J | title = Some physical properties of rutin | journal = Journal of the American Pharmaceutical Association | volume = 41 | issue = 11 | pages = 582–587 | date = November 1952 | pmid = 12999623 | doi = 10.1002/jps.3030411106 }}</ref> |
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| MeltingPtC = 242 |
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| BoilingPtC = |
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| Solubility = insoluble |
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|Section6={{Chembox Pharmacology |
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| ATCCode_prefix = C05 |
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| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 |
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| ATCCode_suffix = CA01 |
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}} |
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|Section7={{Chembox Hazards |
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| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0 |
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'''Rutin''', also called '''rutoside''', '''quercetin-3-O-rutinoside''' and '''sophorin''', is a [[citrus]] [[flavonoid]] [[glycoside]] found in [[buckwheat]],<ref>{{cite journal |
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| author=Kreft S, Knapp M, Kreft I |
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| title=Extraction of rutin from buckwheat (''Fagopyrum esculentum Moench'') seeds and determination by capillary electrophoresis |
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| journal=J. Agric. Food Chem. |
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| volume=47 |
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| issue=11 |
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| pages=4649–52 |
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| date=November 1999 |
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| pmid=10552865 |
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| doi=10.1021/jf990186p |
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}}</ref> the leaves and [[Petiole (botany)|petiole]]s of ''[[Rhubarb|Rheum]]'' species, and [[asparagus]]. Rutin is also found in the fruit of the [[Dimorphandra mollis|fava d'anta]] tree (from [[Brazil]]), fruits and flowers of the [[pagoda tree]], fruits and fruit rinds (especially citrus fruits ([[orange (fruit)|orange]], [[grapefruit]], [[lemon]], [[Lime (fruit)|lime]])) and berries such as [[mulberry]], [[ash tree]] fruits and [[Cranberry|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.<ref>http://www.herbalextractsplus.com/rutin.cfm</ref> |
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Rutin is the [[glycoside]] |
'''Rutin''' ('''rutoside''', '''quercetin-3-O-rutinoside''' or '''sophorin''') is the [[glycoside]] combining the [[flavonol]] [[quercetin]] and the [[disaccharide]] [[rutinose]] (α-<small>L</small>-rhamnopyranosyl-(1→6)-β-<small>D</small>-glucopyranose). It is a [[flavonoid glycoside]] found in a wide variety of plants, including [[citrus]]. |
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== Occurrences == |
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==Chemical relatives== |
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Rutin is one of the [[polyphenol|phenolic compounds]] found in the plant species ''[[Carpobrotus edulis]]''. Its name comes from the name of ''[[Ruta graveolens]]'', a plant that also contains rutin. Various citrus [[Peel (fruit)|fruit peels]] contain 32 to 49 mg/g of [[flavonoid]]s expressed as rutin equivalents.<ref name="Wang">{{cite journal | last1=Wang | first1=Yuan-Chuen | last2=Chuang | first2=Yueh-Chueh | last3=Hsu | first3=Hsing-Wen | title=The flavonoid, carotenoid and pectin content in peels of citrus cultivated in Taiwan | journal=Food Chemistry | volume=106 | issue=1 | year=2008 | issn=0308-8146 | doi=10.1016/j.foodchem.2007.05.086 | pages=277–284}}</ref> Citrus leaves contain rutin at concentrations of 11 and 7 g/kg in orange and lime trees, respectively.<ref name="Soares">{{cite journal | last1=Soares | first1=Márcio Santos | last2=da Silva | first2=Danielle Fernandes | last3=Forim | first3=Moacir Rossi | last4=da Silva | first4=Maria Fátima das Graças Fernandes | last5=Fernandes | first5=João Batista | last6=Vieira | first6=Paulo Cezar | last7=Silva | first7=Denise Brentan | last8=Lopes | first8=Norberto Peporine | last9=de Carvalho | first9=Sérgio Alves | last10=de Souza | first10=Alessandra Alves | last11=Machado | first11=Marcos Antônio | title=Quantification and localization of hesperidin and rutin in ''Citrus sinensis'' grafted on ''C. limonia'' after ''Xylella fastidiosa'' infection by HPLC-UV and MALDI imaging mass spectrometry | journal=Phytochemistry| volume=115 | year=2015 | issn=0031-9422 | pmid=25749617 | doi=10.1016/j.phytochem.2015.02.011 | pages=161–170| bibcode=2015PChem.115..161S }}</ref> In 2021, [[Samoa|Samoan]] researchers identified rutin in the native plant ''matalafi'' (''[[Psychotria insularum]]'').<ref>{{cite journal | vauthors = Molimau-Samasoni S, Woolner VH, Foliga ST, Robichon K, Patel V, Andreassend SK, Sheridan JP, Te Kawa T, Gresham D, Miller D, Sinclair DJ, La Flamme AC, Melnik AV, Aron A, Dorrestein PC, Atkinson PH, Keyzers RA, Munkacsi AB | display-authors = 6 | title = Functional genomics and metabolomics advance the ethnobotany of the Samoan traditional medicine "matalafi" | journal = Proceedings of the National Academy of Sciences of the United States of America | volume = 118 | issue = 45 | pages = e2100880118 | date = November 2021 | pmid = 34725148 | doi = 10.1073/pnas.2100880118 | pmc = 8609454 | bibcode = 2021PNAS..11800880M | s2cid = 240423413 | doi-access = free }}</ref> |
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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.<ref name="naturalstandard">http://www.naturalstandard.com/index-abstract.asp?create-abstract=/monographs/herbssupplements/patient-rutin.asp</ref> |
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== Metabolism == |
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The enzyme [[quercitrinase]] found in ''[[Aspergillus flavus]]'' is in the rutin [[catabolism|catabolic pathway]].<ref>{{cite journal | vauthors = Tranchimand S, Brouant P, Iacazio G | title = The rutin catabolic pathway with special emphasis on quercetinase | journal = Biodegradation | volume = 21 | issue = 6 | pages = 833–859 | date = November 2010 | pmid = 20419500 | doi = 10.1007/s10532-010-9359-7 | s2cid = 30101803 }}</ref> |
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It can combine with [[cations]],{{Which?|date=June 2009}} supplying [[nutrient]]s from the [[soil]] to the cells in [[plant]]s.{{Citation needed|date=June 2009}} In humans, it attaches to the iron ion [[Iron|Fe]]<sup>2+</sup>, 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]]. |
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== In food == |
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Furthermore, it has been shown to inhibit ''[[in vitro]]'' the [[vascular endothelial growth factor]]<ref>{{cite journal|author=Luo|author2=et al.|title=Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids|journal=Nutrition and Cancer|year=2008|volume=60|issue=6|pages=800–9|doi=10.1080/01635580802100851|pmid=19005980|last3=King|first3=Sarah M.|last4=Chen|first4=Yi Charlie}}</ref> in subtoxic concentrations, so acts as an inhibitor of [[angiogenesis]]. This finding can be potentially relevant for the control of some [[cancer]]s. |
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Rutin is a [[citrus]] [[flavonoid]] [[glycoside]] found in many plants, including [[buckwheat]],<ref name="Kreft">{{cite journal | vauthors = Kreft S, Knapp M, Kreft I | title = Extraction of rutin from buckwheat (Fagopyrum esculentumMoench) seeds and determination by capillary electrophoresis | journal = Journal of Agricultural and Food Chemistry | volume = 47 | issue = 11 | pages = 4649–4652 | date = November 1999 | pmid = 10552865 | doi = 10.1021/jf990186p }}</ref> the leaves and [[Petiole (botany)|petiole]]s of ''[[Rhubarb|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).<ref name="Kreft"/> Rutin is one of the primary flavonols found in 'clingstone' [[peach]]es.<ref name=Chang>{{cite journal | vauthors = Chang S, Tan C, Frankel EN, Barrett DM | title = Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars | journal = Journal of Agricultural and Food Chemistry | volume = 48 | issue = 2 | pages = 147–151 | date = February 2000 | pmid = 10691607 | doi = 10.1021/jf9904564 }}</ref> It is also found in [[green tea]] infusions.<ref>{{cite journal | vauthors = Malagutti AR, Zuin V, Cavalheiro ÉT, Henrique Mazo L | year = 2006 | title = Determination of Rutin in Green Tea Infusions Using Square-Wave Voltammetry with a Rigid Carbon-Polyurethane Composite Electrode | journal = Electroanalysis | volume = 18 | issue = 10| pages = 1028–1034 | doi = 10.1002/elan.200603496 }}</ref> |
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Approximate rutin content of selected foods, in [[milligrams]] per 100 [[milliliters]]:<ref>{{cite web|url=http://phenol-explorer.eu/contents/polyphenol/296|title=foods in which the polyphenol Quercetin 3-O-rutinoside is found|publisher=Phenol-Explorer v 3.6|date=June 2015}}</ref> |
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==Health effects== |
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{| class="wikitable sortable" |
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While there is a body of evidence for the effects of rutin and [[quercetin]] in |
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mice<ref>{{cite journal|author=Enkhmaa|author2= et al.|pmid=15795425|title=Mulberry (Morus alba L.) leaves and their major flavonol quercetin 3-(6-malonylglucoside) attenuate atherosclerotic lesion development in LDL receptor-deficient mice|journal=J Nutr|year=2005|volume=135|issue=4|pages=729–34|last3=Katsube|first3=T|last4=Kitajima|first4=K|last5=Anuurad|first5=E|last6=Yamasaki|first6=M|last7=Yamane|first7=Y}}</ref>, |
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rats<ref>{{cite journal|author=Santos|author2=et al.|title=HYPOLIPIDAEMIC EFFECTS OF NARINGENIN, RUTIN, NICOTINIC ACID AND THEIR ASSOCIATIONS|journal=Pharmacological Research|volume=40|issue=6|year=1999|pages=493–6|doi=10.1006/phrs.1999.0556|pmid=10660947|last3=Nagem|first3=TJ|last4=Pinto|first4=AS|last5=Oliveira|first5=MG}}</ref>, |
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! scope="col" | Numeric |
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hamsters<ref>{{cite journal|author=Auger|author2=et al.|title=Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation|journal=J Agric Food Chem.|year= 2005|volume=53|issue=6|pages=2015–21|pmid=15769129|doi=10.1021/jf048177q|last3=Gérain|first3=Peggy|last4=Lequeux|first4=Nadine|last5=Bornet|first5=Aurélie|last6=Serisier|first6=Samuel|last7=Besançon|first7=Pierre|last8=Caporiccio|first8=Bertrand|last9=Cristol|first9=Jean-Paul}}</ref> |
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! scope="col" | Alphabetic |
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and rabbits<ref>{{cite journal|author=Juźwiak|author2=et al.|title=Effect of quercetin on experimental hyperlipidemia and atherosclerosis in rabbits|journal=Pharmacol Rep.|year=2005|volume=57|issue=5|pages=604–9|pmid=16227643|last3=Mokrzycki|first3=K|last4=Marchlewicz|first4=M|last5=Białecka|first5=M|last6=Wenda-Rózewicka|first6=L|last7=Gawrońska-Szklarz|first7=B|last8=Droździk|first8=M}}</ref>, |
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as well as [[in vitro]] studies<ref>{{cite journal|author=Shen|author2=et al.|title=In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E2 production|journal=European Journal of Pharmacology|year=2002|volume=446|issue=1–3|pages=187–94|doi=10.1016/S0014-2999(02)01792-2|pmid=12098601|last3=Lin|first3=HY|last4=Huang|first4=HC|last5=Ko|first5=CH|last6=Yang|first6=LL|last7=Chen|first7=YC}}</ref>, |
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| 332 || Capers, spice |
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no clinical studies directly demonstrating significant, positive effects of rutin as dietary supplement in humans exist. |
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| 45 || Olive (black), raw |
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| 36 || Buckwheat, whole grain flour |
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| 32 || Green tea, infusion |
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| 23 || Asparagus, raw |
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| 19 || Black raspberry, raw |
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| 17 || Black tea, infusion |
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| 11 || Red raspberry, raw |
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| 9 || Buckwheat, groats, thermally treated |
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| 6 || Buckwheat, refined flour |
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| 6 || Greencurrant |
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| 6 || Plum, fresh |
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| 5 || Blackcurrant, raw |
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| 4 || Blackberry, raw |
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| 3 || Tomato (cherry), whole, raw |
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| 2 || Prune |
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| 2 || Fenugreek |
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| 2 || Marjoram, dried |
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| 1 || Grape, raisin |
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| 1 || Zucchini, raw |
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| 1 || Apricot, raw |
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| 0 || Apple |
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| 0 || Redcurrant |
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| 0 || Grape (green) |
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| 0 || Tomato, whole, raw |
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==Research== |
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*Rutin inhibits [[platelet]] aggregation,<ref>{{cite journal|author=Navarro-Núñez|author2=et al.|doi=10.1021/jf0723209|title=Apigenin Inhibits Platelet Adhesion and Thrombus Formation and Synergizes with Aspirin in the Suppression of the Arachidonic Acid Pathway|journal=J. Agric. Food Chem.|year=2008|volume=56|issue=9|pages=2970–6|last3=Palomo|first3=M.|last4=Martínez|first4=C.|last5=Vicente|first5=V.|last6=Castillo|first6=J.|last7=Benavente-García|first7=O.|last8=Diaz-Ricart|first8=M.|last9=Escolar|first9=G.|pmid=18410117}}</ref> as well as decreasing capillary permeability, making the blood thinner and improving circulation.{{Citation needed|date=October 2010}} |
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Rutin (rutoside or rutinoside)<ref name="lpi">{{cite web|url=http://lpi.oregonstate.edu/mic/dietary-factors/phytochemicals/flavonoids|title=Flavonoids|publisher=Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, Oregon|date=November 2015|access-date=25 February 2018}}</ref> and other dietary [[flavonol]]s are under preliminary [[clinical research]] for their potential biological effects, such as in reducing [[post-thrombotic syndrome]], [[Chronic venous insufficiency|venous insufficiency]], or [[endothelial dysfunction]], but there was no [[evidence-based medicine|high-quality evidence]] for their safe and effective uses as of 2018.<ref name=lpi/><ref>{{cite journal | vauthors = Morling JR, Broderick C, Yeoh SE, Kolbach DN | title = Rutosides for treatment of post-thrombotic syndrome | journal = The Cochrane Database of Systematic Reviews | volume = 2018 | issue = 11 | pages = CD005625 | date = November 2018 | pmid = 30406640 | pmc = 6517027 | doi = 10.1002/14651858.CD005625.pub4 }}</ref><ref>{{Cite journal|display-authors=3 |last1=Martinez-Zapata |first1=Maria José |last2=Vernooij |first2=Robin Wm |last3=Simancas-Racines |first3=Daniel |last4=Uriona Tuma |first4=Sonia Maria |last5=Stein |first5=Airton T. |last6=Moreno Carriles |first6=Rosa Maria M. |last7=Vargas |first7=Emilio |last8=Bonfill Cosp |first8=Xavier |date=2020-11-03 |title=Phlebotonics for venous insufficiency |journal=The Cochrane Database of Systematic Reviews |volume=2020 |issue=11 |pages=CD003229 |doi=10.1002/14651858.CD003229.pub4 |issn=1469-493X |pmc=8094625 |pmid=33141449}}</ref> A 2020 review indicated that oral rutosides may reduce leg [[edema]] in people with post-thrombotic syndrome, but the risk of [[adverse effect]]s was higher.<ref name="martinez">{{Cite journal|display-authors=3 |last1=Martinez-Zapata |first1=Maria José |last2=Vernooij |first2=Robin Wm |last3=Simancas-Racines |first3=Daniel |last4=Uriona Tuma |first4=Sonia Maria |last5=Stein |first5=Airton T. |last6=Moreno Carriles |first6=Rosa Maria M. |last7=Vargas |first7=Emilio |last8=Bonfill Cosp |first8=Xavier |date=3 November 2020 |title=Phlebotonics for venous insufficiency |journal=The Cochrane Database of Systematic Reviews |volume=2020 |issue=11 |pages=CD003229 |doi=10.1002/14651858.CD003229.pub4 |issn=1469-493X |pmc=8094625 |pmid=33141449}}</ref> |
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*Rutin shows [[anti-inflammatory]] activity in some animal and ''in vitro'' models.<ref>{{cite journal|author=Guardia|author2=et al.|title=Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat|journal=Il Farmaco|volume=56|issue=9|year=2001|pages=683–7|doi=10.1016/S0014-827X(01)01111-9|pmid=11680812|last3=Juarez|first3=AO|last4=Pelzer|first4=LE}}</ref><ref>{{cite journal|author=Chan Hun Jung|author2=et al.|title=Anti-asthmatic action of quercetin and rutin in conscious guinea-pigs challenged with aerosolized ovalbumin|journal=Arch. Pharmacal Research|volume=30|issue=12|pages=1599–1607|url=http://www.springerlink.com/content/3265v57604507v87|doi=10.1007/BF02977330|year=2007|last3=Cho|first3=Chul Hyung|last4=Kim|first4=Chang Jong}}</ref> |
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*Rutin inhibits [[aldose reductase]] activity{{Citation needed|date=October 2010}}. Aldose reductase is an enzyme normally present in the eye and elsewhere in the body. It helps change glucose into the sugar alcohol [[sorbitol]]. |
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*Rutin also strengthens the [[capillary|capillaries]]{{Citation needed|date=October 2010}}, 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.<ref>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, [http://www.springerlink.com/content/0uayqpwqj3gkrr2p/ doi:10.1007/s002280050138]</ref> |
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* Rutin, as [[ferulic acid]], can reduce the cytotoxicity of oxidized [[LDL cholesterol]] and lower the risk of [[heart disease]].{{Citation needed|date=October 2010}} |
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*There is also some evidence that rutin can be used to treat [[hemorrhoids]], [[varicosis]], and [[microangiopathy]].<ref name="naturalstandard" /> |
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*Rutin is also an antioxidant;<ref>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, [http://onlinelibrary.wiley.com/doi/10.1080/15216549700202141/abstract doi:10.1080/15216549700202141]</ref> compared to quercetin, acacetin, morin, hispidulin, hesperidin, and naringin, it was found to be the strongest.<ref>http://www.diet-and-health.net/Supplements/Rutin.html</ref> However, in other trials, the effects of rutin were lower or negligible compared to those of [[quercetin]].<ref>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 [http://onlinelibrary.wiley.com/doi/10.1002/mnfr.200900329/full doi:10.1002/mnfr.200900329]</ref><ref>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, |
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69(12):1839-1851, [http://dx.doi.org/10.1016/j.bcp.2005.03.017 doi:10.1016/j.bcp.2005.03.017]</ref> |
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[[Hydroxyethylrutoside]]s, synthetic hydroxyethyl acetylations of rutin, are used in the treatment of chronic venous insufficiency. |
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As a [[flavonol]] among similar flavonoids, rutin has low [[bioavailability]] due to poor [[Absorption (pharmacology)|absorption]], high [[metabolism]], and rapid [[excretion]] that collectively make its potential for use as a [[drug|therapeutic agent]] limited.<ref name=lpi/> |
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==In veterinary medicine== |
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Rutin has a [[veterinary]] use in the management of [[chylothorax]] in dogs and cats.<ref>{{Cite pmc |1180424}}</ref> |
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== |
==Biosynthesis == |
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The biosynthesis pathway of rutin in mulberry (''[[Morus alba]]'' L.) leaves begins with [[phenylalanine]], which produces [[cinnamic acid]] under the action of [[phenylalanine ammonia lyase]] (PAL). Cinnamic acid is catalyzed by cinnamic acid-4-hydroxylase (C4H) and [[4-coumarate-CoA ligase]] (4CL) to form ''p''-[[coumaroyl-CoA]]. Subsequently, [[chalcone synthase]] (CHS) catalyzes the condensation of ''p''-coumaroyl-CoA and three molecules of [[malonyl-CoA]] to produce [[naringenin chalcone]], which is eventually converted into naringenin flavanone with the participation of [[chalcone isomerase]] (CHI). With the action of flavanone 3-hydroxylas (F3H), [[dihydrokaempferol]] (DHK) is generated. DHK can be further hydroxylated by flavonoid 3´-hydroxylase (F3'H) to produce [[dihydroquercetin]] (DHQ), which is then catalyzed by [[flavonol synthase]] (FLS) to form [[quercetin]]. After quercetin is catalyzed by UDP-glucose flavonoid 3-''O''-glucosyltransferase ([[UFGT]]) to form [[isoquercitrin]], finally, the formation of rutin from isoquercitrin is catalyzed by flavonoid 3-''O''-glucoside L-rhamnosyltransferase.<ref>{{Cite web |url=http://www.phcog.com/text.asp?2020/16/69/441/286752 |title=Yu X, Liu J, Wan J, Zhao L, Liu Y, Wei Y, Ouyang Z. Cloning, prokaryotic expression, and enzyme activity of a UDP-glucose flavonoid 3-o-glycosyltransferase from mulberry (Morus alba L.) leaves. Phcog Mag 2020;16:441-7 |access-date=2021-06-02 |archive-date=2022-02-16 |archive-url=https://web.archive.org/web/20220216200254/https://www.phcog.com/text.asp?2020/16/69/441/286752 |url-status=dead }}</ref> |
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{{Refimprove|date=October 2010}} |
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{{reflist|2}} |
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[[File:Rutin Biosynthesis.svg|600px]] |
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== References == |
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{{reflist}} |
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== External links == |
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*{{Commonscat-inline}} |
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{{Flavonol}} |
{{Flavonol}} |
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{{Vasoprotectives}} |
{{Vasoprotectives}} |
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[[Category: |
[[Category:CYP3A4 inhibitors]] |
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[[Category: |
[[Category:Quercetin glycosides]] |
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[[Category: |
[[Category:Flavonol rutinosides]] |
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[[Category:Flavonoid antioxidants]] |
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[[ |
[[Category:Polyphenols]] |
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[[de:Rutin]] |
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[[es:Rutina (flavonoide)]] |
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[[eo:Rutino (kemio)]] |
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[[fr:Rutoside]] |
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[[hr:Rutin]] |
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[[it:Rutina]] |
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[[he:רוטין]] |
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[[hu:Rutin (vegyület)]] |
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[[nl:Rutine]] |
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[[ja:ルチン]] |
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[[pl:Rutyna]] |
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[[pt:Rutina]] |
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[[ru:Рутозид]] |
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[[sk:Rutín]] |
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[[sl:Rutin]] |
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[[fi:Rutiini]] |