Rutin: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 455039901

| Name = Rutin

| ImageFile = Rutin structure.svg

| ImageSize = 250px

| ImageName = Rutin

| ImageName2 = Rutin 3D

| IUPACName = 3′,4′,5,7-Tetrahydroxy-3-[α-<small>L</small>-rhamnopyranosyl-(1→6)-β-<small>D</small>-glucopyranosyloxy]flavone

| SystematicName = (4²''S'',4³''R'',4⁴''S'',4⁵''S'',4⁶''R'',7²''R'',7³''R'',7⁴''R'',7⁵''R'',7⁶''S'')-1³,1⁴,2⁵,2⁷,4³,4⁴,4⁵,7³,7⁴,7⁵-Decahydroxy-7⁶-methyl-2⁴''H''-3,6-dioxa-2(2,3)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphane-2⁴-one

| 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

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 153-18-4

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444362

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG = C05625

| PubChem = 5280805

| RTECS = VM2975000

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB01698

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5G06TVY3R7

| 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

| 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

|Section2={{Chembox Properties

| C=27 | H=30 | O=16

| Appearance = Solid

| Density =

| MeltingPtC = 242

| BoilingPtC =

| 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>

|Section6={{Chembox Pharmacology

| ATCCode_prefix = C05

| ATCCode_suffix = CA01

}}

|Section7={{Chembox Hazards

| NFPA-H = 2 | NFPA-F = 0 | NFPA-R = 0

'''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]].

== Occurrences ==

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>

== Metabolism ==

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>

== In food ==

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>

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>

{| class="wikitable sortable"

|+ Sortable table

|-

! scope="col" | Numeric

! scope="col" | Alphabetic

|-

| 332 || Capers, spice

|-

| 45 || Olive (black), raw

|-

| 36 || Buckwheat, whole grain flour

|-

| 32 || Green tea, infusion

|-

| 23 || Asparagus, raw

|-

| 19 || Black raspberry, raw

|-

| 17 || Black tea, infusion

|-

| 11 || Red raspberry, raw

|-

| 9 || Buckwheat, groats, thermally treated

|-

| 6 || Buckwheat, refined flour

|-

| 6 || Greencurrant

|-

| 6 || Plum, fresh

|-

| 5 || Blackcurrant, raw

|-

| 4 || Blackberry, raw

|-

| 3 || Tomato (cherry), whole, raw

|-

| 2 || Prune

|-

| 2 || Fenugreek

|-

| 2 || Marjoram, dried

|-

| 1 || Grape, raisin

|-

| 1 || Zucchini, raw

|-

| 1 || Apricot, raw

|-

| 0 || Apple

|-

| 0 || Redcurrant

|-

| 0 || Grape (green)

|-

| 0 || Tomato, whole, raw

|}

==Research==

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>

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/>

==Biosynthesis ==

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>

[[File:Rutin Biosynthesis.svg|600px]]

== References ==

{{reflist}}

== External links ==

*{{Commonscat-inline}}

[[Category:CYP3A4 inhibitors]]

[[Category:Quercetin glycosides]]

[[Category:Flavonol rutinosides]]

[[Category:Flavonoid antioxidants]]

[[Category:Polyphenols]]