Quercitrin

Last updated
Quercitrin
Quercitrin.png
Quercitrin 3D BS.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 mark.svgN
    Key: OXGUCUVFOIWWQJ-HQBVPOQASA-N X mark.svgN
  • 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.

Contents

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

Occurrence

Quercitrin is a constituent of the dye quercitron. It can be found in Tartary buckwheat ( Fagopyrum tataricum ) [1] and in oaks species like the North American white oak ( Quercus alba ) and English oak ( Quercus robur ). [2] It is also found in Nymphaea odorata or Taxillus kaempferi . [3]

Metabolism

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

Related Research Articles

<span class="mw-page-title-main">Buckwheat</span> Species of flowering plant in the family Polygonaceae

Buckwheat, or common buckwheat, is a flowering plant in the knotweed family Polygonaceae cultivated for its grain-like seeds and as a cover crop. The name "buckwheat" is used for several other species, such as Fagopyrum tataricum, a domesticated food plant raised in Asia.

<i>Quercus robur</i> Species of flowering plant in the beech and oak family Fagaceae

Quercus robur, the pedunculate oak, is a species of flowering plant in the beech and oak family, Fagaceae. It is a large tree, native to most of Europe and western Asia, and is widely cultivated in other temperate regions. It grows on circumneutral soils in the lowlands and is notable for its value to natural ecosystems, supporting a very wide diversity of herbivorous insects and other pests, predators and pathogens.

A glucoside is a glycoside that is chemically derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes.

<span class="mw-page-title-main">Glycoside</span> Molecule in which a sugar is bound to another functional group

In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. These can be activated by enzyme hydrolysis, which causes the sugar part to be broken off, making the chemical available for use. Many such plant glycosides are used as medications. Several species of Heliconius butterfly are capable of incorporating these plant compounds as a form of chemical defense against predators. In animals and humans, poisons are often bound to sugar molecules as part of their elimination from the body.

<span class="mw-page-title-main">Quercitron</span> Natural dye from the bark of the species Quercus velutina

Quercitron is a yellow natural dye obtained from the bark of the Eastern Black Oak, a forest tree indigenous in North America. It was formerly called Dutch pink, English pink, or Italian pink.

<i>Fagopyrum</i> Genus of flowering plants

The genus Fagopyrum is in the flowering plant family Polygonaceae. It includes some important food plants, such as F. esculentum (buckwheat) and F. tataricum. The genus is native to the Indian subcontinent, much of Indochina, and central and southeastern China. Species have been widely introduced elsewhere, throughout the Holarctic and parts of Africa and South America.

<span class="mw-page-title-main">Quercetin</span> Chemical compound

Quercetin is a plant flavonol from the flavonoid group of polyphenols. It is found in many fruits, vegetables, leaves, seeds, and grains; capers, red onions, and kale are common foods containing appreciable amounts of it. It has a bitter flavor and is used as an ingredient in dietary supplements, beverages, and foods.

<i>Fagopyrum tataricum</i> Species of plant

Fagopyrum tataricum, also known as Tartary buckwheat, green buckwheat, ku qiao, Tatar buckwheat, or bitter buckwheat, is a domesticated food plant in the genus Fagopyrum in the family Polygonaceae. With another species in the same genus, common buckwheat, it is often counted as a cereal, but the buckwheats are not closely related to true cereals.

<span class="mw-page-title-main">Rutin</span> Chemical compound

Rutin, also called rutoside, quercetin-3-O-rutinoside and sophorin, is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid found in a wide variety of plants, including citrus.

In enzymology, a quercitrinase (EC 3.2.1.66) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Orientin</span> Chemical compound

Orientin is a flavone, a chemical flavonoid-like compound. It is the 8-C glucoside of luteolin.

<span class="mw-page-title-main">Hyperoside</span> Chemical compound

Hyperoside is a chemical compound. It is the 3-O-galactoside of quercetin.

<span class="mw-page-title-main">Fagopyrin</span> Chemical compound

Fagopyrin is a term used for several closely related naturally occurring substances in the buckwheat plant. Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin.

<span class="mw-page-title-main">Glucogallin</span> Chemical compound

Glucogallin is chemical compound formed from gallic acid and β-D-glucose. It can be found in oaks species like the North American white oak, European red oak and Amla fruit.

<span class="mw-page-title-main">5-Deoxyinositol</span> Chemical compound

5-Deoxyinositol (quercitol) is a cyclitol. It can be found in wines aged in oak wood barrels. It can also be found in Quercus sp. (oaks) and in Gymnema sylvestre. It is different from quercetol, a synonym of quercetin.

Tergallic acids are trimers of gallic acid, often found naturally in the form of glycosides. Tergallic acid O- or C-glucosides that can be found in acorns of several Quercus (oak) species. The dehydrated tergallic acid C-glucoside and tergallic acid O-glucoside can be characterised in the acorns of Quercus macrocarpa. Dehydrated tergallic-C-glucoside can be found in the cork from Quercus suber.

<i>Taxillus kaempferi</i> Species of mistletoe

Taxillus kaempferi is a parasitic plant species in the genus Taxillus found in China, Bhutan and Japan. Its host is Pinus thunbergii.

<span class="mw-page-title-main">Taxillusin</span> Chemical compound

Taxillusin is a flavonol found in the parasitic plant Taxillus kaempferi. It is a galloylated 3-O-glucoside of quercetin.

<i>Fagopyrum cymosum</i> Species of grass

Fagopyrum cymosum, also known as tall buckwheat, is a domesticated plant used in traditional Chinese medicine, for animal feed, and as an ornamental plant. It is native to much of China, and to Bhutan, Nepal, India, Burma, and Vietnam.

<span class="mw-page-title-main">2-Hydroxybenzylamine</span>

2-Hydroxybenzylamine is a natural product found in Himalayan tartary buckwheat. It acts as an antioxidant and scavanger of free radicals and isolevuglandins and is sold as a dietary supplement.

References

  1. 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
  2. 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
  3. 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

Audah, K.A.; Ettin, J.; Darmadi, J.; Azizah, N.N.; Anisa, A.S.; Hermawan, T.D.F.; Tjampakasari, C.R.; Heryanto, R.; Ismail, I.S.; Batubara, I. Indonesian Mangrove Sonneratia caseolaris Leaves Ethanol Extract Is a Potential Super Antioxidant and Anti Methicillin-Resistant Staphylococcus aureus Drug. Molecules 2022, 27, 8369. https://doi.org/10.3390/molecules27238369