Flavonol 3-O-glucosyltransferase

Flavonol 3-O-glucosyltransferase
Identifiers
EC no.2.4.1.91
CAS no.50812-18-5
Databases
BRENDAenzyme data
ExPASyNiceZyme view
KEGGenzyme entry
MetaCycmetabolic pathway
Rheareactions
PDB structuresRCSB PDB PDBe PDBsum
Gene OntologyAmiGO / QuickGO
Search
PMCarticles
PubMedarticles
NCBIproteins

Flavonol 3-O-glucosyltransferase (EC 2.4.1.91) is an enzyme that catalyzes the general chemical reaction

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

The two substrates of this enzyme are UDP-glucose and a flavonol. Its products are uridine diphosphate (UDP) and the corresponding 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.

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.

Occurrence

Flavonol 3-O-glucosyltransferase is found in grapes (Vitis vinifera), parsley, snapdragons (Antirrhinum majus), kale (Brassica oleracea), tulip bulbs, peony, and grapefruit (Citrus x paradisi).

Function

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. For example, it converts quercetin to isoquercetin:

A glucose unit is transferred from UDP-glucose to a specific hydroxy group of the flavonol, with uridine diphosphate (UDP) as a byproduct. By the same mechanism, the enzyme converts anthocyanidins to anthocyanins as a part of the phenylpropanoid pathway. For example, pelargonidin is transformed into callistephin (pelargonidin 3-O-glucoside).

+ UDP-glucose
 
 
 
UDP
Rightward reaction arrow with minor product(s) to top right
 
 
 

This enzyme is also involved in the flavone glycoside pathway, and daphnetin modification in some organisms.

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.

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. The primary active site residue of this enzyme is Asp181, as determined by studies of how mutations affect enzyme capacity. There are several documentations of the crystalline structure of flavonol 3-O-glucosyltransferase (2C1X, 2C1Z, and 2C9Z), and, based on these renderings of the enzyme, there is only one subunit in the quaternary structure of the molecule.

References

  1. 1 2 Kleinehollenhorst, G.; Behrens, H.; Pegels, G.; Srunk, N.; Wiermann, R. (1982). "Formation of Flavonol 3-O-Diglycosides and Flavonol 3-O-Triglycosides by Enzyme Extracts from Anthers of Tulipa cv. Apeldoorn / Characterization and Activity of Three Different O -Glycosyltransferases during Anther Development". Zeitschrift für Naturforschung C. 37 (7–8): 587–599. doi:10.1515/znc-1982-7-808.
  2. ↑ Dooner, H. K.; Nelson, O. E. (1977). "Genetic control of UDPglucose:flavonol 3-O-glucosyltransferase in the endosperm of maize". Biochemical Genetics. 15 (5–6): 509–519. doi:10.1007/BF00520194. PMID 880210.
  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. Bibcode:2001PlnSc.160..543K. doi:10.1016/S0168-9452(00)00425-8. PMID 11166442.
  4. ↑ Sutter A, Grisebach H (1973). "UDP-glucose: flavonol 3-0-glucosyltransferase from cell suspension cultures of parsley". Biochim. Biophys. Acta. 309 (2): 289–95. doi:10.1016/0005-2744(73)90027-2. PMID 4731963.
  5. ↑ Wiermann R (1982). "Formation of flavonol 3-O-diglycosides and flavonol 3-O-triglycosides by enzyme extracts from anthers of Tulipa cv apeldoorn - characterization and activity of 3 different O-glycosyltransferases during anther development". Z. Naturforsch. C. 37: 587–599. doi:10.1515/znc-1982-7-808. S2CID 37241803.
  6. 1 2 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.
  7. ↑ "BRENDA - Information on EC 2.4.1.91 - flavonol 3-O-glucosyltransferase".
  8. 1 2 Enzyme 2.4.1.91 at KEGG Pathway Database.
  9. ↑ 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.
  10. ↑ 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.
  11. ↑ 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.