Rutin
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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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Preferred 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, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside combining the flavonol quercetin and the disaccharide rutinose (α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranose). It is a citrus flavonoid found in a wide variety of plants including citrus.
Occurrences
Rutin is one of the phenolic compounds found in the invasive plant species Carpobrotus edulis and contributes to the antibacterial[3] properties of the plant.
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.[4]
Citrus leaves contain rutin at concentrations of 11 and 7 g/kg in orange and lime trees respectively.[5]
In 2021, Samoan researchers identified rutin in the native plant "matalafi" (Psychotria insularum).[6][7]
Metabolism
The enzyme quercitrinase can be found in Aspergillus flavus.[8] It is an enzyme in the rutin catabolic pathway.[9]
In food
Rutin is a citrus flavonoid glycoside found in many plants including buckwheat,[10] 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).[10] Rutin is one of the primary flavonols found in 'clingstone' peaches.[11] It is also found in green tea infusions.[12]
Approximate rutin content per 100g of selected foods, in milligrams per 100 milliliters:[13]
Numeric | Alphabetic |
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332 | Capers, spice |
45 | Olive [Black], raw |
36 | Buckwheat, whole grain flour |
23 | Asparagus, raw |
19 | Black raspberry, raw |
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 |
2 | Tea (Black), infusion |
1 | Grape, raisin |
1 | Zucchini, raw |
1 | Apricot, raw |
1 | Tea (Green), infusion |
0 | Apfel |
0 | Redcurrant |
0 | Grape (green) |
0 | Tomato, whole, raw |
Forschung
Rutin (rutoside or rutinoside)[14] 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.[14][15][16][needs update] 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.[14]
in 2021 in vitro studies reported that Rutin is a low micromolar Inhibitor of SARS-CoV-2 Main Protease 3CLpro[17] but antiviral activity in infected cells was not detected, confirming that the pharmakinetic represent the main limiting issue for the use of this molecules as a potential drug.[18]
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.[19]
References
- ^ Merck Index, 12th Edition, 8456
- ^ Krewson CF, Naghski J (November 1952). "Some physical properties of rutin". Journal of the American Pharmaceutical Association. American Pharmaceutical Association. 41 (11): 582–587. doi:10.1002/jps.3030411106. PMID 12999623.
- ^ van der Watt E, Pretorius JC (June 2001). "Purification and identification of active antibacterial components in Carpobrotus edulis L". Journal of Ethnopharmacology. 76 (1): 87–91. doi:10.1016/S0378-8741(01)00197-0. PMID 11378287.
- ^ [1] p. 280 Table 1
- ^ [2] p.8 fig. 7
- ^ Molimau-Samasoni S, Woolner VH, Foliga ST, Robichon K, Patel V, Andreassend SK, et al. (November 2021). "Functional genomics and metabolomics advance the ethnobotany of the Samoan traditional medicine "matalafi"". Proceedings of the National Academy of Sciences of the United States of America. 118 (45): e2100880118. doi:10.1073/pnas.2100880118. PMID 34725148. S2CID 240423413.
- ^ "Plant in traditional Samoa medicine could be as effective as ibuprofen, study shows". TheGuardian.com. 4 November 2021.
- ^ quercitrinase on www.brenda-enzymes.org
- ^ Tranchimand S, Brouant P, Iacazio G (November 2010). "The rutin catabolic pathway with special emphasis on quercetinase". Biodegradation. 21 (6): 833–859. doi:10.1007/s10532-010-9359-7. PMID 20419500. S2CID 30101803.
- ^ a b Kreft S, Knapp M, Kreft I (November 1999). "Extraction of rutin from buckwheat (Fagopyrum esculentumMoench) seeds and determination by capillary electrophoresis". Journal of Agricultural and Food Chemistry. 47 (11): 4649–4652. doi:10.1021/jf990186p. PMID 10552865.
- ^ Chang S, Tan C, Frankel EN, Barrett DM (February 2000). "Low-density lipoprotein antioxidant activity of phenolic compounds and polyphenol oxidase activity in selected clingstone peach cultivars". Journal of Agricultural and Food Chemistry. 48 (2): 147–151. doi:10.1021/jf9904564. PMID 10691607.
- ^ Malagutti AR, Zuin V, Cavalheiro ÉT, Henrique Mazo L (2006). "Determination of Rutin in Green Tea Infusions Using Square-Wave Voltammetry with a Rigid Carbon-Polyurethane Composite Electrode". Electroanalysis. 18 (10): 1028–1034. doi:10.1002/elan.200603496.
- ^ "foods in which the polyphenol Quercetin 3-O-rutinoside is found". Phenol-Explorer v 3.6. June 2015.
- ^ a b c "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, Oregon. November 2015. Retrieved 25 February 2018.
- ^ Morling JR, Broderick C, Yeoh SE, Kolbach DN (November 2018). "Rutosides for treatment of post-thrombotic syndrome". The Cochrane Database of Systematic Reviews. 11 (11): CD005625. doi:10.1002/14651858.CD005625.pub4. PMC 6517027. PMID 30406640.
- ^ Martinez-Zapata MJ, Vernooij RW, Uriona Tuma SM, Stein AT, Moreno RM, Vargas E, et al. (April 2016). "Phlebotonics for venous insufficiency". The Cochrane Database of Systematic Reviews. 4: CD003229. doi:10.1002/14651858.CD003229.pub3. PMC 7173720. PMID 27048768.
- ^ Rizzuti B, Grande F, Conforti F, Jimenez-Alesanco A, Ceballos-Laita L, Ortega-Alarcon D, et al. (April 2021). "Rutin Is a Low Micromolar Inhibitor of SARS-CoV-2 Main Protease 3CLpro: Implications for Drug Design of Quercetin Analogs". Biomedicines. 9 (4): 375. doi:10.3390/biomedicines9040375. PMC 8066963. PMID 33918402.
{{cite journal}}
: CS1 maint: unflagged free DOI (link) - ^ Sancineto L, Ostacolo C, Ortega-Alarcon D, Jimenez-Alesanco A, Ceballos-Laita L, Vega S, et al. (October 2021). "l-Arginine Improves Solubility and ANTI SARS-CoV-2 Mpro Activity of Rutin but Not the Antiviral Activity in Cells". Molecules. 26 (19): 6062. doi:10.3390/molecules26196062. PMC 8512140. PMID 34641606.
{{cite journal}}
: CS1 maint: unflagged free DOI (link) - ^ 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
External links
- Media related to Rutin at Wikimedia Commons