Glucogallin
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| 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 | |
13405-60-2  | |
| ChemSpider | 26333268  |
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| Jmol-3D images | Image |
| PubChem | 124021 |
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| Properties | |
| Molecular formula |
C13H16O10 |
| Molar mass | 332.26 g·mol−1 |
| Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |
| verify (what is: /?) | |
| 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). 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. doi:10.1016/0014-5793(82)81244-1.
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