Rhea - reaction knowledgebase

Enzymes

UniProtKB ^help_outline	2 proteins
Enzyme class ^help_outline	EC 2.4.1.194 4-hydroxybenzoate 4-O-beta-D-glucosyltransferase
GO Molecular Function ^help_outline	GO:0047250 4-hydroxybenzoate 4-O-beta-D-glucosyltransferase activity

Reaction participants Show >> << Hide

Name ^help_outline 4-hydroxybenzoate Identifier CHEBI:17879 (Beilstein: 3589159; CAS: 456-23-5) ^help_outline Charge -1 Formula C7H5O3 InChIKey^help_outline FJKROLUGYXJWQN-UHFFFAOYSA-M SMILES^help_outline Oc1ccc(cc1)C([O-])=O 2D coordinates Mol file for the small molecule Search links Involved in 30 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline UDP-α-D-glucose Identifier CHEBI:58885 (Beilstein: 3827329) ^help_outline Charge -2 Formula C15H22N2O17P2 InChIKey^help_outline HSCJRCZFDFQWRP-JZMIEXBBSA-L SMILES^help_outline OC[C@H]1O[C@H](OP([O-])(=O)OP([O-])(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)n2ccc(=O)[nH]c2=O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 223 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline 4-(β-D-glucosyloxy)benzoate Identifier CHEBI:11935 Charge -1 Formula C13H15O8 InChIKey^help_outline XSSDYIMYZONMBL-BZNQNGANSA-M SMILES^help_outline OC[C@H]1O[C@@H](Oc2ccc(cc2)C([O-])=O)[C@H](O)[C@@H](O)[C@@H]1O 2D coordinates Mol file for the small molecule Search links Involved in 1 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline H⁺ Identifier CHEBI:15378 Charge 1 Formula H InChIKey^help_outline GPRLSGONYQIRFK-UHFFFAOYSA-N SMILES^help_outline [H+] 2D coordinates Mol file for the small molecule Search links Involved in 9,176 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule
Name ^help_outline UDP Identifier CHEBI:58223 Charge -3 Formula C9H11N2O12P2 InChIKey^help_outline XCCTYIAWTASOJW-XVFCMESISA-K SMILES^help_outline O[C@@H]1[C@@H](COP([O-])(=O)OP([O-])([O-])=O)O[C@H]([C@@H]1O)n1ccc(=O)[nH]c1=O 2D coordinates Mol file for the small molecule Search links Involved in 542 reaction(s) Find molecules that contain or resemble this structure Find proteins in UniProtKB for this molecule

Cross-references

	RHEA:15153	RHEA:15154	RHEA:15155	RHEA:15156
Reaction direction	undefined	left-to-right	right-to-left	bidirectional
UniProtKB ^help_outline	2 proteins
EC numbers ^help_outline	2.4.1.194
Gene Ontology ^help_outline	GO:0047250
KEGG ^help_outline				R01304
MetaCyc ^help_outline		2.4.1.194-RXN

Publications

Two UGT84 Family Glycosyltransferases Catalyze a Critical Reaction of Hydrolyzable Tannin Biosynthesis in Pomegranate (Punica granatum).

Ono N.N., Qin X., Wilson A.E., Li G., Tian L.

Hydrolyzable tannins (HTs) play important roles in plant herbivore deterrence and promotion of human health. A critical step in HT production is the formation of 1-O-galloyl-β-D-glucopyranoside (β-glucogallin, ester-linked gallic acid and glucose) by a UDP-glucosyltransferase (UGT) activity. We cl ... >> More

Hydrolyzable tannins (HTs) play important roles in plant herbivore deterrence and promotion of human health. A critical step in HT production is the formation of 1-O-galloyl-β-D-glucopyranoside (β-glucogallin, ester-linked gallic acid and glucose) by a UDP-glucosyltransferase (UGT) activity. We cloned and biochemically characterized four candidate UGTs from pomegranate (Punica granatum), of which only UGT84A23 and UGT84A24 exhibited β-glucogallin forming activities in enzyme assays. Although overexpression and single RNAi knockdown pomegranate hairy root lines of UGT84A23 or UGT84A24 did not lead to obvious alterations in punicalagin (the prevalent HT in pomegranate) accumulation, double knockdown lines of the two UGTs resulted in largely reduced levels of punicalagins and bis-hexahydroxydiphenyl glucose isomers. An unexpected accumulation of galloyl glucosides (ether-linked gallic acid and glucose) was also detected in the double knockdown lines, suggesting that gallic acid was utilized by an unidentified UGT activity for glucoside formation. Transient expression in Nicotiana benthamiana leaves and immunogold labeling in roots of pomegranate seedlings collectively indicated cytosolic localization of UGT84A23 and UGT84A24. Overall, functional characterization and localization of UGT84A23 and UGT84A24 open up opportunities for further understanding the regulatory control of HT metabolism in plants and its coordination with other biochemical pathways in the metabolic network. << Less

PLoS ONE 11:E0156319-E0156319(2016) [PubMed] [EuropePMC]

Comments

Published in: Katsumata, T., Shige, H. and Ejiri, S.-I. Biochemical-studies on pollen. 34. UDP glucose-4-(beta-D-glucopyranosyloxy) benzoic-acid glucosyltransferase from the pollen of Pinus densiflora. Phytochemistry 28 (1989) 359–362.