Names | |
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IUPAC name
3′,4′,5,7-Tetrahydroxy-3-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranosyloxy]flavone
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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 | |
3D model (
JSmol)
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ChemSpider | |
DrugBank | |
ECHA InfoCard | 100.005.287 |
KEGG | |
PubChem
CID
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RTECS number |
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UNII | |
CompTox Dashboard (
EPA)
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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 their
standard state (at 25 °C [77 °F], 100 kPa).
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Rutin (rutoside, quercetin-3-O-rutinoside or sophorin) is the glycoside combining the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is a flavonoid glycoside found in a wide variety of plants, including citrus.
Rutin is one of the phenolic compounds found in the invasive plant species, Carpobrotus edulis. Its name comes from the name of Ruta graveolens, a plant that also contains rutin. Various citrus fruit peels contain 32 to 49 mg/g of flavonoids expressed as rutin equivalents. [3] Citrus leaves contain rutin at concentrations of 11 and 7 g/kg in orange and lime trees, respectively. [4] In 2021, Samoan researchers identified rutin in the native plant matalafi ( Psychotria insularum). [5]
The enzyme quercitrinase found in Aspergillus flavus is in the rutin catabolic pathway. [6]
Rutin is a citrus flavonoid glycoside found in many plants, including buckwheat, [7] 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). [7] Rutin is one of the primary flavonols found in 'clingstone' peaches. [8] It is also found in green tea infusions. [9]
Approximate rutin content per 100g of selected foods, in milligrams per 100 milliliters: [10]
Numeric | Alphabetic |
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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 |
Rutin (rutoside or rutinoside) [11] and other dietary flavonols are under preliminary clinical research for their potential biological effects, such as in reducing post-thrombotic syndrome, venous insufficiency, or endothelial dysfunction, but there was no high-quality evidence for their safe and effective uses as of 2018. [11] [12] [13] A 2020 review indicated that oral rutosides may reduce leg edema in people with post-thrombotic syndrome, but the risk of adverse effects was higher. [14]
As a flavonol among similar flavonoids, rutin has low bioavailability due to poor absorption, high metabolism, and rapid excretion that collectively make its potential for use as a therapeutic agent limited. [11]
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. [15]