Glucogallin: Difference between revisions
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'''Glucogallin''' is chemical compound formed from [[gallic acid]] and [[glucose|β-<small>D</small>-glucose]]. It can be found in oaks species like the North American white oak (''[[Quercus alba]]'') |
'''Glucogallin''' is chemical compound formed from [[gallic acid]] and [[glucose|β-<small>D</small>-glucose]]. It can be found in oaks species like the North American white oak (''[[Quercus alba]]''), European red oak (''[[Quercus robur]]'').<ref>{{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}}</ref> and Amla fruit ([[Emblica officinalis]]) <ref>{{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 }}</ref>. |
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It is formed by a [[gallate 1-beta-glucosyltransferase]] (UDP-glucose: gallate glucosyltransferase), an enzyme performing the [[esterification]] of two substrates, [[UDP-glucose]] and [[gallic acid|gallate]] to yield two products, [[Uridine diphosphate|UDP]] and glucogallin. This enzyme can be found in [[oak]] leaf preparations.<ref>{{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}}</ref> |
It is formed by a [[gallate 1-beta-glucosyltransferase]] (UDP-glucose: gallate glucosyltransferase), an enzyme performing the [[esterification]] of two substrates, [[UDP-glucose]] and [[gallic acid|gallate]] to yield two products, [[Uridine diphosphate|UDP]] and glucogallin. This enzyme can be found in [[oak]] leaf preparations.<ref>{{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}}</ref> |
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Revision as of 14:52, 8 February 2014
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| Names | |
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| IUPAC name
[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl]3,4,5-trihydroxybenzoate
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| Other names
β-Glucogallin
1-Galloylglucose 1-Galloyl-β-glucose 1-O-Galloyl-β-D-glucose beta-Glucogallin Monogalloyl glucose | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.242.331 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C13H16O10 | |
| Molar mass | 332.261 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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.
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.
{{cite journal}}: CS1 maint: unflagged free DOI (link) - ^ 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.