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

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1,2,3,4,6-Pentagalloyl glucose
Chemical structure of pentagalloyl glucose
Names
IUPAC name
β-D-Glucopyranose pentakis(3,4,5-trihydroxybenzoate)
Systematic IUPAC name
(2S,3R,4S,5R,6R)-6-{[(3,4,5-Trihydroxybenzoyl)oxy]methyl}oxane-2,3,4,5-tetrayl tetrakis(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
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
 100.113.489 Edit this at Wikidata
UNII
  • 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 checkY
    Key: QJYNZEYHSMRWBK-NIKIMHBISA-N checkY
  • 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 940.681 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 checkY☒N ?)

1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.[1]

Pentagalloyl glucose can precipitate proteins,

salivary α-amylase.[3]

Natural occurrence

1,2,3,4,6-Pentagalloyl glucose can be found in

Paeonia suffruticosa (Tree Peony),.,[7] Mangifera indica (mango) [8] and Bouea macrophylla Griffith (maprang).[9]

Biosynthesis

The enzyme

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

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.[10]

Research

Pentagalloyl glucose has been studied for its potential use as an

antidiabetic, and antioxidant.[11] It has also been studied for radioprotection.[5] This compound helps stabilize the elastin and collagen in vascular tissues[12] and restores the biomechanical properties of arterial ECM.[13] In addition, pentagalloyl glucose has shown to reduce arterial calcification and helps promote extracellular matrix preservation in animal models of abdominal aortic aneurysm.[14] In vitro studies with mouse C2C12 myoblast cells have shown the PGG helps in lowering reactive oxygen species (ROS) and matrix metalloproteinase-2 (MMP-2) expression in a dose-dependent manner. [15]

References

  1. PMID 2757399
    .
  2. doi:10.1021/jf971097k
    .
  3. PMID 19038368
    .
  4. doi:10.1016/S0031-9422(00)83125-8
    .
  5. ^
    S2CID 44278609
    .
  6. ^
    doi:10.1016/S0031-9422(98)00014-4
    .
  7. S2CID 205620592
    .
  8. S2CID 102513001
    .
  9. PMID 32382295
    .
  10. S2CID 85098105
    .
  11. doi:10.1016/j.jff.2017.07.045
    .
  12. PMID 30298373
    .
  13. PMID 31277241
    .
  14. PMID 33435461
    .
  15. S2CID 235199265
    .
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