Pentagalloylglucose
Chemical compound
From Wikipedia, the free encyclopedia
Pentagalloylglucose, or more specifically 1,2,3,4,6-penta-O-galloyl-β-D-glucose, is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.[1]
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| Names | |
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| 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) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.113.489 |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C41H32O26 | |
| Molar mass | 940.681 g·molâ1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Pentagalloylglucose can precipitate proteins,[2] including human salivary α-amylase.[3]
Natural occurrence
Pentagalloylglucose can be found in Punica granatum (pomegranate),[4] Elaeocarpus sylvestris,[5] Rhus typhina (Staghorn sumac),[6] Paeonia suffruticosa (Tree Peony),[7] Mangifera indica (mango) [8] and Bouea macrophylla Griffith (maprang).[9]
Biosynthesis
The enzyme beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase uses 1-O-galloyl-β-D-glucose and 1,2,3,6-tetrakis-O-galloyl-β-D-glucose to produce D-glucose and pentagalloylglucose.
Metabolism
Tellimagrandin II is formed from pentagalloylglucose 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 (hexagalloylglucose).[6]
Chemistry
Pentagalloylglucose can undergo oxidation reactions which are depending on the pH.[10]
Research
Pentagalloylglucose has been studied for its potential use as an antimicrobial, anti-inflammatory, anticarcinogenic, 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, pentagalloylglucose 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]