Pentagalloylglucose
chemical compound
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.
Pentagalloylglucose can precipitate proteins, including human salivary α-amylase.
Natural occurrence
Pentagalloylglucose can be found in Punica granatum (pomegranate), Elaeocarpus sylvestris, Rhus typhina (Staghorn sumac), Paeonia suffruticosa (Tree Peony), Mangifera indica (mango) and Bouea macrophylla Griffith (maprang).
Biosynthesis
The enzyme beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase catalyzes the chemical reaction which transfers the fifth and final gallic acid unit to a central glucose molecule to form pentagalloylglucose.
The enzyme was characterised from oak (Quercus robur).
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).
Chemistry
Pentagalloylglucose can undergo oxidation reactions which are depending on the pH.
Research
Pentagalloylglucose has been studied for its potential use as an antimicrobial, anti-inflammatory, anticarcinogenic, antidiabetic, and antioxidant. It has also been studied for radioprotection.
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