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| Names | |
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| IUPAC name 3′,4′,5,7-Tetrahydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavone | |
| Systematic IUPAC name (42S,43R,44S,45S,46R,72R,73R,74R,75R,76S)-13,14,25,27,43,44,45,73,74,75-Decahydroxy-76-methyl-24H-3,6-dioxa-2(2,3)-[1]benzopyrana-4(2,6),7(2)-bis(oxana)-1(1)-benzenaheptaphane-24-one | |
| Other names Rutoside(INN) Phytomelin Sophorin Birutan Eldrin Birutan Forte Rutin trihydrate Globularicitrin Violaquercitrin Quercetin rutinoside | |
| Identifiers | |
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3D model (JSmol) | |
| ChemSpider |
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| DrugBank |
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| ECHA InfoCard | 100.005.287 |
| KEGG |
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| RTECS number |
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| Properties | |
| C27H30O16 | |
| Molar mass | 610.521 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 (fire diamond) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Rutin (rutoside,quercetin-3-O-rutinoside orsophorin) is theglycoside combining theflavonolquercetin and thedisacchariderutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is aflavonoid glycoside found in a wide variety of plants, includingcitrus.
Rutin is one of thephenolic compounds found in the plant speciesCarpobrotus edulis. Its name comes from the name ofRuta graveolens, a plant that also contains rutin. Various citrusfruit peels contain 32 to 49 mg per g offlavonoids expressed as rutin equivalents.[3] Citrus leaves contain rutin at concentrations of 11 g per kg in orange trees and 7 g per kg in lime trees.[4]In 2021,Samoan researchers identified rutin in the native plantmatalafi (Psychotria insularum).[5]
The enzymequercitrinase found inAspergillus flavus is in the rutincatabolic pathway.[6]
Rutin is acitrusflavonoidglycoside found in many plants, includingbuckwheat,[7] the leaves andpetioles ofRheum species, andasparagus.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).[7] Rutin is one of the primary flavonols found in 'clingstone'peaches.[8] It is also found ingreen tea infusions.[9]
Approximate rutin content of selected foods, inmilligrams per 100 grams ormilliliters:[10]
| Numeric | Alphabetic |
|---|---|
| 389[11] | Tartary buckwheat, roasted bran |
| 332 | Capers, spice |
| 68[11] | Tartary buckwheat, roasted grain |
| 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 |
Rutin (rutoside or rutinoside)[12] and other dietaryflavonols are under preliminaryclinical research for their potential biological effects, such as in reducingpost-thrombotic syndrome,venous insufficiency, orendothelial dysfunction, but there remains nohigh-quality evidence for their safe and effective uses, as of 2018.[12][13][14] A 2020 review indicated that oral rutosides may reduce legedema by a small amount in people with post-thrombotic syndrome, but the risk ofadverse effects was higher.[15]
As aflavonol among similar flavonoids, rutin has lowbioavailability due to poorabsorption, highmetabolism, and rapidexcretion that collectively make its biological properties in vivo difficult to study, and its potential for use as atherapeutic agent limited.[12]
The biosynthesis pathway of rutin in mulberry (Morus alba L.) leaves begins withphenylalanine, which producescinnamic acid under the action ofphenylalanine ammonia lyase (PAL). Cinnamic acid is catalyzed by cinnamic acid-4-hydroxylase (C4H) and4-coumarate-CoA ligase (4CL) to formp-coumaroyl-CoA. Subsequently,chalcone synthase (CHS) catalyzes the condensation ofp-coumaroyl-CoA and three molecules ofmalonyl-CoA to producenaringenin chalcone, which is eventually converted into naringenin flavanone with the participation ofchalcone 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 producedihydroquercetin (DHQ), which is then catalyzed byflavonol synthase (FLS) to formquercetin. After quercetin is catalyzed by UDP-glucose flavonoid 3-O-glucosyltransferase (UFGT) to formisoquercitrin, finally, the formation of rutin from isoquercitrin is catalyzed by flavonoid 3-O-glucoside L-rhamnosyltransferase.[16]
Media related toRutin at Wikimedia CommonsFlavonols and their conjugates | |||||||||
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| Backbone |
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| O-Methylated flavonols |
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| Pyranoflavonols |
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| Furanoflavonols |
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| Semisynthetic |
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