Glucogallin

Glucogallin
Names

IUPAC name [(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]3,4,5-trihydroxybenzoate
Other names β-Glucogallin 1-Galloylglucose 1-Galloyl-β-glucose 1-O-Galloyl-β-D-glucose beta-Glucogallin Monogalloyl glucose
Identifiers
CAS Number	13405-60-2^Y
ChemSpider	26333268^N
Jmol interactive 3D	Image
PubChem	124021
InChI InChI=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^N Key: KGHSLXLLBHRMML-VKISENBKSA-N^N 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 Key: KGHSLXLLBHRMML-VKISENBKBE
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
Properties
Chemical formula	C₁₃H₁₆O₁₀
Molar mass	332.26 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is ^YN ?)
Infobox references

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) ^[1] and Amla fruit (Emblica officinalis).^[2]

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.^[3]

This the first step in the biosynthesis of gallotannins. The molecule is then used by enzymes in the gallotannins synthetis 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

↑ Mämmelä, Pirjo; Savolainen, Heikki; Lindroos, Lasse; Kangas, Juhani; Vartiainen, Terttu (2000). "Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry". Journal of Chromatography A 891 (1): 75–83. doi:10.1016/S0021-9673(00)00624-5. PMID 10999626.
↑ Puppala, M; Ponder, J; Suryanarayana, P; Reddy, GB; Petrash, JM; LaBarbera, DV (2012). "The isolation and characterization of β-glucogallin as a novel aldose reductase inhibitor from Emblica officinalis.". PLOS ONE 7 (4): e31399. doi:10.1371/journal.pone.0031399.
↑ Gross, G.G. (1982). "Synthesis of β-glucogallin from UDP-glucose and gallic acid by an enzyme preparation from oak leaves". FEBS Letters 148: 67–70. doi:10.1016/0014-5793(82)81244-1.

Types of gallotannins

Aglycones

Galloyl glucoses

1-Galloyl glucose Glucogallin

Digalloyl glucoses:	1,6-Digalloyl glucose 2,6-Digalloyl glucose 3,6-digalloyl glucose

Trigalloyl glucoses:	1,2,3-Trigalloyl glucose 1,2,3-tri-O-galloyl-β-D-glucose 1,2,6-Trigalloyl glucose / 1,3,6-Trigalloyl glucose

Tetragalloyl glucoses:	1,2,3,6-tetragalloylglucose 1,2,3,6-tetra-O-galloyl-β-D-glucose 1,2,4,6-Tetragalloyl glucose 1,2,4,6-tetra-O-galloyl-β-D-glucose

Pentagalloyl glucose:	1,2,3,4,6-Pentagalloyl-glucose 6-digalloyl-1,2,3-trigalloyl-glucose

other	Hexagalloyl glucose Heptagalloyl glucose Octagalloyl glucose Nonagalloyl glucose Decagalloyl glucose

Galloyl quinic acids

Galloyl quinic acids:	3-O-Galloylquinic acid theogallin 4-O-Galloylquinic acid 5-O-Galloylquinic acid

Digalloyl quinic acids:	1,4-Di-O-galloylquinic acid 3,4-di-O-Galloylquinic acid 3,5-di-O-Galloylquinic acid 4,5-di-O-Galloylquinic acid

Trigalloyl quinic acids:	1,3,4-Tri-O-galloylquinic acid 3,4,5-Tri-O-galloylquinic acid

Galloyl shikimic acids

4-O-Galloyl shikimic acid
5-O-Galloyl shikimic acid
3,5-di-O-galloyl-shikimic acid
3,4,5-tri-O-galloylshikimic acid

others

1,2,6-trigalloyl alloside
1,3,6-trigalloyl alloside
1,2,3,6-tetragalloyl alloside
1-O-galloyl proto-quercitol
1,4-di-O-galloyl proto-quercitol

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