glucogallin

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 441142282

| Name = Glucogallin

| ImageFile = Glucogallin.svg

| ImageName = Chemical structure of β-glucogallin

| ImageAlt = Chemical structure of β-glucogallin

| IUPACName = [(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]3,4,5-trihydroxybenzoate

| OtherNames = β-Glucogallin
1-Galloylglucose
1-Galloyl-β-glucose
1-O-Galloyl-β-D-glucose
beta-Glucogallin
Monogalloyl glucose

|Section1={{Chembox Identifiers

| CASNo = 13405-60-2

| CASNo_Ref = {{cascite|correct|??}}

| CASNoOther =

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 4X7JGS9BFY

| PubChem = 124021

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 26333268

| SMILES = CO[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)c2cc(c(c(c2)O)O)O)O)O)O

| InChI = 1/C13H16O10/c1-21-12-9(18)8(17)10(19)13(23-12)22-11(20)4-2-5(14)7(16)6(15)3-4/h2-3,8-10,12-19H,1H3/t8-,9-,10+,12-,13+/m0/s1

| InChIKey = KGHSLXLLBHRMML-VKISENBKBE

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 1S/C13H16O10/c1-21-12-9(18)8(17)10(19)13(23-12)22-11(20)4-2-5(14)7(16)6(15)3-4/h2-3,8-10,12-19H,1H3/t8-,9-,10+,12-,13+/m0/s1

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = KGHSLXLLBHRMML-VKISENBKSA-N

| MeSHName =

}}

|Section2={{Chembox Properties

| C=13 | H=16 | O=10

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

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 (Quercus alba), European red oak (Quercus robur) {{cite journal | doi = 10.1016/S0021-9673(00)00624-5 | title = Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry | year = 2000 | last1 = Mämmelä | first1 = Pirjo | last2 = Savolainen | first2 = Heikki | last3 = Lindroos | first3 = Lasse | last4 = Kangas | first4 = Juhani | last5 = Vartiainen | first5 = Terttu | journal = Journal of Chromatography A | volume = 891 | pages = 75–83 | pmid = 10999626 | issue = 1}} and Amla fruit (Phyllanthus emblica).{{cite journal | doi = 10.1371/journal.pone.0031399 | title = The isolation and characterization of β-glucogallin as a novel aldose reductase inhibitor from Emblica officinalis. | year = 2012 | last1 = Puppala | first1 = M | last2 = Ponder | first2 = J | last3 = Suryanarayana | first3 = P | last4 = Reddy | first4 = GB | last5 = Petrash | first5 = JM | last6 = LaBarbera | first6 = DV | journal = PLOS ONE | volume = 7 | issue = 4 | pages=e31399 | pmid=22485126 | pmc=3317655| bibcode = 2012PLoSO...731399P | doi-access = free }}

It is formed by a gallate 1-beta-glucosyltransferase (UDP-glucose: gallate glucosyltransferase), an enzyme performing the esterification of two substrates, UDP-glucose and gallate to yield two products, UDP and glucogallin. This enzyme can be found in oak leaf preparations.{{cite journal | doi = 10.1016/0014-5793(82)81244-1 | title = Synthesis of β-glucogallin from UDP-glucose and gallic acid by an enzyme preparation from oak leaves | year = 1982 | last1 = Gross | first1 = G.G. | journal = FEBS Letters | volume = 148 | pages = 67–70| s2cid = 86402007 | doi-access = free }}

This the first step in the biosynthesis of gallotannins. The molecule is then used by enzymes in the gallotannins synthetics pathway like beta-glucogallin O-galloyltransferase or beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase.

β-Glucogallin is aldose reductase inhibitor.

Half-life of β-Glucogallin in human body seems to be unknown.

References

Category:Gallotannins