Rutin Explained

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.

Occurrences

Rutin is one of the 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 fruit peels contain 32 to 49 mg/g of flavonoids expressed as rutin equivalents.[1] Citrus leaves contain rutin at concentrations of 11 and 7 g/kg in orange and lime trees, respectively.[2] In 2021, Samoan researchers identified rutin in the native plant matalafi (Psychotria insularum).[3]

Metabolism

The enzyme quercitrinase found in Aspergillus flavus is in the rutin catabolic pathway.[4]

In food

Rutin is a citrus flavonoid glycoside found in many plants, including buckwheat,[5] 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).[5] Rutin is one of the primary flavonols found in 'clingstone' peaches.[6] It is also found in green tea infusions.[7]

Approximate rutin content of selected foods, in milligrams per 100 milliliters:[8]

Sortable table
NumericAlphabetic
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)[9] 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.[9] [10] [11] 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.[12]

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.[9]

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.[13]

Notes and References

  1. Wang . Yuan-Chuen . Chuang . Yueh-Chueh . Hsu . Hsing-Wen . The flavonoid, carotenoid and pectin content in peels of citrus cultivated in Taiwan . Food Chemistry . 106 . 1 . 2008 . 0308-8146 . 10.1016/j.foodchem.2007.05.086 . 277–284.
  2. Soares . Márcio Santos . da Silva . Danielle Fernandes . Forim . Moacir Rossi . da Silva . Maria Fátima das Graças Fernandes . Fernandes . João Batista . Vieira . Paulo Cezar . Silva . Denise Brentan . Lopes . Norberto Peporine . de Carvalho . Sérgio Alves . de Souza . Alessandra Alves . Machado . Marcos Antônio . 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 . Phytochemistry. 115 . 2015 . 0031-9422 . 25749617 . 10.1016/j.phytochem.2015.02.011 . 161–170. 2015PChem.115..161S .
  3. 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 . 6 . 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 . November 2021 . 34725148 . 10.1073/pnas.2100880118 . 8609454 . 2021PNAS..11800880M . 240423413 . free .
  4. Tranchimand S, Brouant P, Iacazio G . The rutin catabolic pathway with special emphasis on quercetinase . Biodegradation . 21 . 6 . 833–859 . November 2010 . 20419500 . 10.1007/s10532-010-9359-7 . 30101803 .
  5. Kreft S, Knapp M, Kreft I . Extraction of rutin from buckwheat (Fagopyrum esculentumMoench) seeds and determination by capillary electrophoresis . Journal of Agricultural and Food Chemistry . 47 . 11 . 4649–4652 . November 1999 . 10552865 . 10.1021/jf990186p .
  6. Chang S, Tan C, Frankel EN, Barrett DM . 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 . February 2000 . 10691607 . 10.1021/jf9904564 .
  7. 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 . 10.1002/elan.200603496 .
  8. Web site: foods in which the polyphenol Quercetin 3-O-rutinoside is found. Phenol-Explorer v 3.6. June 2015.
  9. Web site: Flavonoids. Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, Oregon. November 2015. 25 February 2018.
  10. Morling JR, Broderick C, Yeoh SE, Kolbach DN . Rutosides for treatment of post-thrombotic syndrome . The Cochrane Database of Systematic Reviews . 2018 . 11 . CD005625 . November 2018 . 30406640 . 6517027 . 10.1002/14651858.CD005625.pub4 .
  11. 3 . Martinez-Zapata . Maria José . Vernooij . Robin Wm . Simancas-Racines . Daniel . Uriona Tuma . Sonia Maria . Stein . Airton T. . Moreno Carriles . Rosa Maria M. . Vargas . Emilio . Bonfill Cosp . Xavier . 2020-11-03 . Phlebotonics for venous insufficiency . The Cochrane Database of Systematic Reviews . 2020 . 11 . CD003229 . 10.1002/14651858.CD003229.pub4 . 1469-493X . 8094625 . 33141449.
  12. 3 . Martinez-Zapata . Maria José . Vernooij . Robin Wm . Simancas-Racines . Daniel . Uriona Tuma . Sonia Maria . Stein . Airton T. . Moreno Carriles . Rosa Maria M. . Vargas . Emilio . Bonfill Cosp . Xavier . 3 November 2020 . Phlebotonics for venous insufficiency . The Cochrane Database of Systematic Reviews . 2020 . 11 . CD003229 . 10.1002/14651858.CD003229.pub4 . 1469-493X . 8094625 . 33141449.
  13. Web site: 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 . 2021-06-02 . 2022-02-16 . https://web.archive.org/web/20220216200254/https://www.phcog.com/text.asp?2020/16/69/441/286752 . dead .

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