Flavonol 3-O-glucosyltransferase

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Flavonol 3-O-glucosyltransferase
Flavonol 3-O-glucosyltransferase.jpg
Flavonol 3-O-glucosyltransferase
Identifiers
EC no. 2.4.1.91
CAS no. 50812-18-5
Databases
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MetaCyc metabolic pathway
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In enzymology, a flavonol 3-O-glucosyltransferase (EC 2.4.1.91) is an enzyme that catalyzes the chemical reaction

Contents

UDP-glucose + a flavonol UDP + a flavonol 3-O-beta-D-glucoside

Thus, the two substrates of this enzyme are UDP-glucose and flavonol, whereas its two products are UDP and flavonol 3-O-beta-D-glucoside. The flavonoids that can act as substrates within this reaction include quercetin, kaempferol, dihydrokaempferol, kaempferid, fisetin, and isorhamnetin. Flavonol 3-O-glucosyltransferase is a hexosyl group transfer enzyme. [1]

This enzyme is known by the systematic name UPD-glucose:flavonol 3-O-D glucosyltransferase, and it participates in flavonoid biosynthesis and causes the formation of anthocyanins. Anthocyanins produce a purple color in the plant tissues that they are present in. [2]

It is an enzyme found most notably in grapes ( Vitis vinifera ). [3] This enzyme is found within a number of other plants as well—such as snapdragons ( Antirrhinum majus ), kale ( Brassica oleracea ), and grapefruit ( Citrus x paradisi ). [4]

Pathways

This enzyme is involved in the biosynthesis of secondary metabolites. The primary function of this enzyme within its pathway is binding a glucoside onto a flavonol molecule, forming a flavonol 3-O-glucoside. [5] It is through this mechanism that the enzyme converts anthocyanidins to anthocyanins as a part of the phenylpropanoid pathway. One specific example would be this enzymes actions on pelargonidin. Flavonol 3-O-glucosyltransferase binds the glucoside to this protein, making pelargonidin 3-O-glucoside. This enzyme is also involved in the flavone glycoside pathway, and daphnetin modification in some organisms. The role of the enzyme in these pathways is, again, to bind a glucoside to the substrate to construct a flavonol 3-O-glucoside. [6]

The structure of pelargonidin. Pelargonidin.png
The structure of pelargonidin.
The structure of pelargonidin 3-O-glucoside. Pelargonidin 3-O-glucoside.svg
The structure of pelargonidin 3-O-glucoside.

Nomenclature

This enzyme belongs to the family of glycosyltransferases, specifically the hexosyltransferases. The systematic name of this enzyme class is UDP-glucose:flavonol 3-O-D-glucosyltransferase. Other names in common use include:

Among those, UFGT is divided into UDP-glucose: Flavonoid 3-O-glucosyltransferase (UF3GT) and UDP-glucose: Flavonoid 5-O-glucosyltransferase (UF5GT), which are responsible for the glucosylation of anthocyanins to produce stable molecules. [7]

Inhibitors and Structure of the Enzyme

Some of the inhibitors of this enzyme include CaCl2, CoCl2, Cu+2, CuCl2, KCl, Mg+2, and Mn+2. [8] The primary active site residue of this enzyme is Asp181, as determined by studies of how mutations affect enzyme capacity. [9] There are several documentations of the crystalline structure of flavonol 3-O-glucosyltransferase (2C1X, 2C1Z, and 2C9Z), [10] and, based on these renderings of the enzyme, there is only one subunit in the quaternary structure of the molecule.

Related Research Articles

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

Rutin is the glycoside combining the flavonol quercetin and the disaccharide rutinose. It is a flavonoid glycoside found in a wide variety of plants, including citrus.

In enzymology, a leucocyanidin oxygenase (EC 1.14.11.19) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Flavonoid biosynthesis</span>

Flavonoids are synthesized by the phenylpropanoid metabolic pathway in which the amino acid phenylalanine is used to produce 4-coumaroyl-CoA. This can be combined with malonyl-CoA to yield the true backbone of flavonoids, a group of compounds called chalcones, which contain two phenyl rings. Conjugate ring-closure of chalcones results in the familiar form of flavonoids, the three-ringed structure of a flavone. The metabolic pathway continues through a series of enzymatic modifications to yield flavanones → dihydroflavonols → anthocyanins. Along this pathway, many products can be formed, including the flavonols, flavan-3-ols, proanthocyanidins (tannins) and a host of other various polyphenolics.

In enzymology, an anthocyanidin 3-O-glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an anthocyanin 3'-O-beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a cyanidin 3-O-rutinoside 5-O-glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a flavonol-3-O-glucoside glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a flavonol-3-O-glucoside L-rhamnosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a flavonol-3-O-glycoside glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a flavonol 7-O-beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a hydroquinone glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, an isoflavone 7-O-glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a nuatigenin 3beta-glucosyltransferase is an enzyme that catalyzes the chemical reaction

In enzymology, a sarsasapogenin 3β-glucosyltransferase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Pelargonidin</span> Red anthocyanidin pigment found in certain flowers and fruits

Pelargonidin is an anthocyanidin, a type of plant pigment producing a characteristic orange color used in food and industrial dyes.

<span class="mw-page-title-main">Anthocyanin</span> Class of chemical compounds

Anthocyanins, also called anthocyans, are water-soluble vacuolar pigments that, depending on their pH, may appear red, purple, blue, or black. In 1835, the German pharmacist Ludwig Clamor Marquart gave the name Anthokyan to a chemical compound that gives flowers a blue color for the first time in his treatise "Die Farben der Blüthen". Food plants rich in anthocyanins include the blueberry, raspberry, black rice, and black soybean, among many others that are red, blue, purple, or black. Some of the colors of autumn leaves are derived from anthocyanins.

<span class="mw-page-title-main">Phenolic content in wine</span> Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

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

Petunidin (Pt), like Europinidin and Malvidin, is derived from Delphinidin and is an O-methylated anthocyanidin of the 3-hydroxy type. It is a natural organic compound, a dark-red or purple water-soluble pigment found in many redberries including chokeberries, Saskatoon berries or different species of grape, and also part of the pigments responsible for the petal colors in many flowers. This pigment gives the Indigo Rose tomatoes the majority of their deep purple color when the fruits are exposed to sunlight. The name of the molecule itself is derived from the word Petunia.

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

Laricitrin is an O-methylated flavonol, a type of flavonoid. It is found in red grape and in Vaccinium uliginosum. It is one of the phenolic compounds present in wine.

Anthocyanin 5-O-glucosyltransferase is an enzyme that forms anthocyanin 3,5-O-diglucoside from anthocyanin 3-O-glucoside.

References

  1. http://brenda-enzymes.info/enzyme.php?ecno=2.4.1.91&Suchword=&reference=&organism%5B%5D=Vitis+vinifera&show_tm=0#REACTION TYPE
  2. Dooner, H.K. & Nelson, O.E. Biochem Genet (1977) 15: 509. doi : 10.1007/BF00520194
  3. Kobayashi S, Ishimaru M, Ding CK, Yakushiji H, Goto N (February 2001). "Comparison of UDP-glucose:flavonoid 3-O-glucosyltransferase (UFGT) gene sequences between white grapes (Vitis vinifera) and their sports with red skin". Plant Sci. 160 (3): 543–550. doi:10.1016/S0168-9452(00)00425-8. PMID   11166442.
  4. "BRENDA - Information on EC 2.4.1.91 - flavonol 3-O-glucosyltransferase".
  5. http://brenda-enzymes.info/enzyme.php?ecno=2.4.1.91&Suchword=&reference=&organism%5B%5D=Vitis+vinifera&show_tm=0#SOURCE TISSUE
  6. "KEGG ENZYME: 2.4.1.115". www.genome.jp. Retrieved 2016-12-06.
  7. Zhao DQ, Han CX, Ge JT, Tao J (November 2012). "Isolation of a UDP-glucose: Flavonoid 5-O-glucosyltransferase gene and expression analysis of anthocyanin biosynthetic genes in herbaceous peony (Paeonia lactiflora Pall.)". Electronic Journal of Biotechnology. 15 (6). doi: 10.2225/vol15-issue6-fulltext-7 .
  8. Schomburg, Professor Dietmar; Schomburg, Dr Ida, eds. (1 January 2006). "Flavonol 3-O-glucosyltransferase". Springer Handbook of Enzymes. Vol. 32. Springer Berlin Heidelberg. pp. 21–29. doi:10.1007/978-3-540-49534-5_2. ISBN   978-3-540-32591-8.
  9. Hiromoto, Takeshi; Honjo, Eijiro; Noda, Naonobu; Tamada, Taro; Kazuma, Kohei; Suzuki, Masahiko; Blaber, Michael; Kuroki, Ryota (2016-12-06). "Structural basis for acceptor-substrate recognition of UDP-glucose: anthocyanidin 3-O-glucosyltransferase from Clitoria ternatea". Protein Science. 24 (3): 395–407. doi:10.1002/pro.2630. ISSN   0961-8368. PMC   4353365 . PMID   25556637.
  10. Offen, W; Martinez-Fleites, C; Yang, M; Kiat-Lim, E; Davis, B.G; Tarling, C.A; Ford, C.M; Bowles, D.J; Davies, G.J. (2006-01-01). "Structure of a Flavonoid Glucosyltransferase Reveals the Basis for Plant Natural Product Modification". EMBO J. 25 (6): 1396–405. doi:10.1038/sj.emboj.7600970. PMC   1422153 . PMID   16482224.

Further reading