Glucogallin

Glucogallin
Chemical structure of β-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 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 26333268 ☒N
ECHA InfoCard 100.242.331 Edit this at Wikidata
PubChem CID
  • 124021
UNII
  • 4X7JGS9BFY checkY
CompTox Dashboard (EPA)
  • DTXSID00928396 Edit this at Wikidata
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
  • 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 332.261 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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Infobox references
Chemical compound

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 (Phyllanthus emblica).[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 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

  1. ^ 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.
  2. ^ 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. Bibcode:2012PLoSO...731399P. doi:10.1371/journal.pone.0031399. PMC 3317655. PMID 22485126.
  3. ^ 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. S2CID 86402007.
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Types of gallotannins
AglyconesGalloyl glucoses
  • 1-Galloyl glucose
    • Glucogallin
Digalloyl glucoses:
Trigalloyl glucoses:
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:
other
  • Hexagalloyl glucose
  • Heptagalloyl glucose
  • Octagalloyl glucose
  • Nonagalloyl glucose
  • Decagalloyl glucose
Galloyl quinic acids
Galloyl quinic acids:
  • 3-O-Galloylquinic acid
  • 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:
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