Glucogallin

Glucogallin
Chemical structure of β-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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.242.331
KEGG
UNII
  • 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 checkY
    Key: KGHSLXLLBHRMML-VKISENBKSA-N checkY
  • 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
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).
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 (Phyllanthus emblica).[2]

It is formed as the first step in the biosynthesis of gallotannins in a pathway using the enzymes beta-glucogallin O-galloyltransferase and beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase.

β-Glucogallin is aldose reductase inhibitor.

Biosynthesis and metabolism

Glucogalllin is formed by the enzyme gallate 1-beta-glucosyltransferase which forms the glucosyl derivative of gallic acid using UDP-glucose as the source of the transferred sugar unit giving uridine diphosphate (UDP) as byproduct. This enzyme can be found in oak leaf preparations.[3]

The enzyme beta-glucogallin O-galloyltransferase takes two molecules of glucogallin and gives one of the gallotannin, 1,6-digalloylglucose, and one of D-glucose. The product 1,6-digalloylglucose can react with another unit of glucogallin to give 1,2,6-trigalloylglucose.[4]

2 Glucogallin
 
 
 
 
Rightward reaction arrow
 
 
 
2D representation of the chemical structure of 1,6-Digalloylglucose .
1,6-Digalloylglucose
+
 
2D representation of the chemical structure of Q23905964.
D-glucose

By a similar mechanism, additional glucogallin units are added until β-penta-O-galloyl-glucose is formed.[5]

β-penta-O-galloyl-glucose

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.
  4. ↑ Denzel K, Schilling G, Gross GG (1988). "Biosynthesis of gallotannins - enzymatic conversion of 1,6-digalloylglucose to 1,2,6-trigalloylglucose". Planta. 176 (1): 135–137. Bibcode:1988Plant.176..135D. doi:10.1007/BF00392489. PMID 24220744.
  5. ↑ Cammann J, Denzel K, Schilling G, Gross GG (1989). "Biosynthesis of gallotannins: beta-glucogallin-dependent formation of 1,2,3,4,6-pentagalloylglucose by enzymatic galloylation of 1,2,3,6-tetragalloylglucose". Arch. Biochem. Biophys. 273 (1): 58–63. doi:10.1016/0003-9861(89)90161-6. PMID 2757399.
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