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


1,2,3,4,6-Pentagalloylglucose is the pentagallic acid ester of glucose. It is a gallotannin and the precursor of ellagitannins.
Pentagalloyl glucose can precipitate proteins, including human salivary α-amylase.

Natural occurrence

1,2,3,4,6-Pentagalloyl glucose can be found in Punica granatum, Elaeocarpus sylvestris, Rhus typhina, Paeonia suffruticosa,., Mangifera indica and Bouea macrophylla Griffith.

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

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

Chemistry

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

Research

Pentagalloyl glucose has been studied for its potential use as an antimicrobial, anti-inflammatory, anticarcinogenic, antidiabetic, and antioxidant. It has also been studied for radioprotection. This compound helps stabilize the elastin and collagen in vascular tissues and restores the biomechanical properties of arterial ECM.