Rutin

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Rutin
Rutin
Names
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
3D model (
JSmol
)
ChemSpider
DrugBank
ECHA InfoCard
 100.005.287 Edit this at Wikidata
KEGG
RTECS number
  • VM2975000
UNII
  • 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
  • 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
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)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 0: Will not burn. E.g. waterInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
0
0
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

flavonoid glycoside 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. 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]

Metabolism

The enzyme quercitrinase found in Aspergillus flavus is in the rutin catabolic pathway.[6]

In food

Rutin is a

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

milliliters:[10]

Sortable table
Numeric 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)

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]

Biosynthesis

The biosynthesis pathway of rutin in mulberry (

isoquercitrin, finally, the formation of rutin from isoquercitrin is catalyzed by flavonoid 3-O-glucoside L-rhamnosyltransferase.[15]

References

  1. ^ Merck Index, 12th Edition, 8456
  2. PMID 12999623
    .
  3. ISSN 0308-8146
    .
  4. PMID 25749617
    .
  5. S2CID 240423413
    .
  6. S2CID 30101803
    .
  7. ^
    PMID 10552865
    .
  8. PMID 10691607
    .
  9. doi:10.1002/elan.200603496
    .
  10. ^ "foods in which the polyphenol Quercetin 3-O-rutinoside is found". Phenol-Explorer v 3.6. June 2015.
  11. ^ a b c "Flavonoids". Micronutrient Information Center, Linus Pauling Institute, Oregon State University, Corvallis, Oregon. November 2015. Retrieved 25 February 2018.
  12. PMID 30406640
    .
  13. PMID 33141449
    .
  14. PMID 33141449
    .
  15. ^ "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". Archived from the original on 2022-02-16. Retrieved 2021-06-02.

External links

  • Media related to Rutin at Wikimedia Commons
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