Quercitrin

Quercitrin
Names
IUPAC name
3′,4′,5,7-Tetrahydroxy-3-(α-L-rhamnopyranosyloxy)flavone
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-1-benzopyran-4-one
Other names
Quercetin 3-O-a-L-rhamnoside
Thujin
Quercetin 3-rhamnoside
Quercetin-3-rhamnoside
Quercetin-3-L-rhamnoside
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.567 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1 X markN
    Key: OXGUCUVFOIWWQJ-HQBVPOQASA-N X markN
  • InChI=1/C21H20O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-18,21-26,28-29H,1H3/t7-,15-,17+,18+,21-/m0/s1
    Key: OXGUCUVFOIWWQJ-HQBVPOQABA
  • C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C=C4)O)O)O)O)O
Properties
C21H20O11
Molar mass 448.38 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose.

Austrian chemist Heinrich Hlasiwetz (1825-1875) is remembered for his chemical analysis of quercitrin.

It has also been investigated as a potential dietary supplement.

Occurrence

Quercitrin is a constituent of the dye quercitron. It can be found in Tartary buckwheat (Fagopyrum tataricum) and in oaks species like the North American white oak (Quercus alba) and English oak (Quercus robur). It is also found in Nymphaea odorata or Taxillus kaempferi.

Metabolism

The enzyme quercitrinase catalyzes the chemical reaction between quercitrin and H2O to yield L-rhamnose and quercetin.

References

  1. ↑ Audah KA, Ettin J, Darmadi J, Azizah NN, Anisa AS, Hermawan TDF; et al. (2022). "Indonesian Mangrove Sonneratia caseolaris Leaves Ethanol Extract Is a Potential Super Antioxidant and Anti Methicillin-Resistant Staphylococcus aureus Drug". Molecules. 27 (23): 8369. doi:10.3390/molecules27238369. PMC 9735687. PMID 36500458.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ↑ Tartary Buckwheat (Fagopyrum tataricum Gaertn.) as a Source of Dietary Rutin and Quercitrin. Nina Fabjan, Janko Rode, Iztok Jože Košir, Zhuanhua Wang, Zheng Zhang and Ivan Kreft, J. Agric. Food Chem., 2003, 51 (22), pp. 6452–6455, doi:10.1021/jf034543e
  3. ↑ Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry. Pirjo Mämmelä, Heikki Savolainen, Lasse Lindroos, Juhani Kangas and Terttu Vartiainen, Journal of Chromatography A, Volume 891, Issue 1, 1 September 2000, Pages 75-83, doi:10.1016/S0021-9673(00)00624-5
  4. ↑ The constituents of Taxillus kaempferi and the host, Pinus thunbergii. I. Catechins and flavones of Taxillus kaempferi. Konishi T, Nishio T, Kiyosawa S, Fujiwara Y and Konoshima T, Yakugaku Zasshi., February 1996, volume 116, issue 2, pages 148-157 (article in Japanese), doi:10.1248/yakushi1947.116.2_148