1,2,3,4,6-Pentagalloyl glucose

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For other uses, see Pentagalloyl glucose.
1,2,3,4,6-Pentagalloyl glucose
Chemical structure of pentagalloyl glucose
Names
IUPAC name
[(2S,3R,4S,5R,6R)-2,3,5-Tris[(3,4,5-trihydroxybenzoyl)oxy]-6-[(3,4,5-trihydroxybenzoyl)oxymethyl]oxan-4-yl] 3,4,5-trihydroxybenzoate
Other names
1,2,3,4,6-Penta-O-galloyl-β-D-glucose
1,2,3,4,6-Pentakis-O-galloyl-beta-D-glucose
beta-Penta-O-galloyl-glucose
PGG
1,2,3,4,6-Penta-O-galloyl-beta-D-glucose
Identifiers
14937-32-7 N
ChEBI CHEBI:18082 YesY
ChEMBL ChEMBL382408 YesY
ChemSpider 58735 YesY
Jmol 3D model Interactive image
PubChem 65238
  • InChI=1S/C41H32O26/c42-17-1-12(2-18(43)28(17)52)36(57)62-11-27-33(64-37(58)13-3-19(44)29(53)20(45)4-13)34(65-38(59)14-5-21(46)30(54)22(47)6-14)35(66-39(60)15-7-23(48)31(55)24(49)8-15)41(63-27)67-40(61)16-9-25(50)32(56)26(51)10-16/h1-10,27,33-35,41-56H,11H2/t27-,33-,34+,35-,41+/m1/s1 YesY
    Key: QJYNZEYHSMRWBK-NIKIMHBISA-N YesY
  • C1=C(C=C(C(=C1O)O)O)C(=O)OCC2C(C(C(C(O2)OC(=O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O)OC(=O)C6=CC(=C(C(=C6)O)O)O
Properties
C41H32O26
Molar mass 940.68 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 YesYN ?)
Infobox references

1,2,3,4,6-Pentagalloyl glucose is the pentahydroxy gallic acid ester of glucose. It is the common precursor of gallotannins and the related ellagitannins.[1]

Pentagalloyl glucose can precipitate proteins[2] including human salivary α-amylase.[3]

It may also be used in radioprotection.[4]

Natural occurrence

1,2,3,4,6-Pentagalloyl glucose can be found in Punica granatum (pomegranate),[5] Elaeocarpus sylvestris,[4] Rhus typhina (Staghorn sumac),[6] and Paeonia suffruticosa (Tree Peony).[7]

Biosynthesis

The enzyme beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase uses 1-O-galloyl-beta-D-glucose and 1,2,3,6-tetrakis-O-galloyl-beta-D-glucose to produce D-glucose and pentagalloyl glucose.

Metabolism

Metabolism of ellagitannins

Tellimagrandin II is formed from pentagalloyl glucose by oxidative dehydrogenation and coupling of 2 galloyl groups.

β-glucogallin: 1,2,3,4,6-pentagalloyl-β-d-glucose galloyltransferase is an enzyme found in the leaves of Rhus typhina that catalyzes the galloylation of 1,2,3,4,6-penta-O-galloyl-β-D-glucose to 3-O-digalloyl-1,2,4,6-tetra-O-galloyl-β-d-glucose (hexa-galloylglucose).[6]

Chemistry

Pentagalloyl glucose can undergo oxidation reactions which are depending on the pH.[8]

References

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  1. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Mechanisms of protein precipitation for two tannins, pentagalloyl glucose and epicatechin16 (4→8) catechin (procyanidin). Hagerman A. E., Rice M. E. and Ritchard N. T., Journal of agricultural and food chemistry, 1998, vol. 46, no7, pp. 2590-2595
  3. ↑ Evidence for pentagalloyl glucose binding to human salivary α-amylase through aromatic amino acid residues. Gyöngyi Gyémánt, Ágnes Zajácz, Bálint Bécsi, Chandran Ragunath, Narayanan Ramasubbu, Ferenc Erdődi, Gyula Batta and Lili Kandra, Biochimica et Biophysica Acta (BBA) - Proteins & Proteomics, Volume 1794, Issue 2, February 2009, pp. 291-296
  4. ↑ 4.0 4.1 Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ 6.0 6.1 Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Reaction pH and protein affect the oxidation products of β-pentagalloyl glucose. Yumin C. and Hagerman A.E., Free radical research, 2005, vol. 39, no2, pp. 117-124
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