1,2,3,4,6-Pentagalloylglucose is the penta

gallic acid Gallic acid (also known as 3,4,5-trihydroxybenzoic acid) is a trihydroxybenzoic acid with the formula C6 H2( OH)3CO2H. It is classified as a phenolic acid. It is found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. It i ...

ester of

glucose Glucose is a simple sugar with the molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using ...

. It is a

gallotannin A gallotannin is any of a class of molecules belonging to the hydrolysable tannins. Gallotannins are polymers formed when gallic acid, a polyphenol monomer, esterifies and binds with the hydroxyl group of a polyol carbohydrate such as glucose. Meta ...

and the precursor of

ellagitannin The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl group ...

s. 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 The pomegranate (''Punica granatum'') is a fruit-bearing deciduous shrub in the family Lythraceae, subfamily Punicoideae, that grows between tall. The pomegranate was originally described throughout the Mediterranean region. It was introduc ...

'' (pomegranate), '' Elaeocarpus sylvestris'', ''

Rhus typhina ''Rhus typhina'', the staghorn sumac, is a species of flowering plant in the family Anacardiaceae, native to eastern North America. It is primarily found in southeastern Canada, the northeastern and midwestern United States, and the Appalachian M ...

'' (Staghorn sumac), ''

Paeonia suffruticosa Paeonia or Paionia may refer to: * The genus ''Paeonia'', which comprises all peony plants * Paeonia (kingdom), an ancient state occupying roughly the same area as the present-day Republic of North Macedonia * Paionia (municipality) Paionia ( e ...

'' (Tree Peony),., ''

Mangifera indica ''Mangifera indica'', commonly known as mango, is a species of flowering plant in the family Anacardiaceae. It is a large fruit tree, capable of growing to a height of . There are two distinct genetic populations in modern mangoesthe "Indian type ...

'' (

mango A mango is an edible stone fruit produced by the tropical tree ''Mangifera indica''. It is believed to have originated in the region between northwestern Myanmar, Bangladesh, and northeastern India. ''M. indica'' has been cultivated in South a ...

) and ''

Bouea macrophylla ''Bouea macrophylla'', commonly known as gandaria or plum mango or mango plum in English, is a species of flowering plant native to Southeast Asia. The tree belongs to the family Anacardiaceae which also includes mango and cashew. Description ...

'' Griffith ( maprang).

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 Onekama ( ) is a village in Manistee County in the U.S. state of Michigan. The population was 411 at the 2010 census. The village is located on the shores of Portage Lake and is surrounded by Onekama Township. The town's name is derived from "On ...

to produce

D-glucose Glucose is a simple sugar with the Chemical formula#Molecular formula, molecular formula . Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis f ...

and pentagalloyl glucose.

Metabolism

Tellimagrandin II Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in '' Geum japonicum'' and ''Syzygium aromaticum'' (clove).Purification and Characterization of Eugeniin as an Anti-herpesvirus Compoun ...

is formed from pentagalloyl glucose by oxidative

dehydrogenation In chemistry, dehydrogenation is a chemical reaction that involves the removal of hydrogen, usually from an organic molecule. It is the reverse of hydrogenation. Dehydrogenation is important, both as a useful reaction and a serious problem. At ...

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).

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 An antimicrobial is an agent that kills microorganisms or stops their growth. Antimicrobial medicines can be grouped according to the microorganisms they act primarily against. For example, antibiotics are used against bacteria, and antifungals ar ...

anti-inflammatory Anti-inflammatory is the property of a substance or treatment that reduces inflammation or swelling. Anti-inflammatory drugs, also called anti-inflammatories, make up about half of analgesics. These drugs remedy pain by reducing inflammation as o ...

anticarcinogenic An anticarcinogen (also known as a carcinopreventive agent) is a substance that counteracts the effects of a carcinogen or inhibits the development of cancer. Anticarcinogens are different from anticarcinoma agents (also known as anticancer or ant ...

antidiabetic Drugs used in diabetes treat diabetes mellitus by altering the glucose level in the blood. With the exceptions of insulin, most GLP receptor agonists (liraglutide, exenatide, and others), and pramlintide, all are administered orally and are thus ...

, and

antioxidant Antioxidants are compounds that inhibit oxidation, a chemical reaction that can produce free radicals. This can lead to polymerization and other chain reactions. They are frequently added to industrial products, such as fuels and lubricant ...

. 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. In addition, pentagalloyl glucose has shown to reduce arterial calcification and helps promote extracellular matrix preservation in animal models of abdominal aortic aneurysm. ''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.

References

{{DEFAULTSORT:Pentagalloyl glucose, 1, 2, 3, 4, 6- Gallotannins Trihydroxybenzoic acids Pyrogallols