Glucogallin is chemical compound formed from
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 ...
and
β-D-glucose. It can be found in oaks species like the North American white oak (''
Quercus alba
An oak is a tree or shrub in the genus ''Quercus'' (; Latin "oak tree") of the beech family, Fagaceae. There are approximately 500 extant species of oaks. The common name "oak" also appears in the names of species in related genera, notably '' ...
''), European red oak (''
Quercus robur
''Quercus robur'', commonly known as common oak, pedunculate oak, European oak or English oak, is a species of flowering plant in the beech and oak family, Fagaceae. It is a large tree, native plant, native to most of Europe west of the Caucasus ...
'') and Amla fruit (''
Phyllanthus emblica
''Phyllanthus emblica'', also known as emblic, emblic myrobalan, myrobalan, Indian gooseberry, Malacca tree, or amla, from the Sanskrit आमलकी (āmalakī), is a deciduous tree of the family Phyllanthaceae. Its native range is tropical a ...
'').
It is formed by a
gallate 1-beta-glucosyltransferase
In enzymology, a gallate 1-beta-glucosyltransferase () is an enzyme that catalyzes the chemical reaction
:UDP-glucose + gallate \rightleftharpoons UDP + 1-galloyl-beta-D-glucose
Thus, the two substrates of this enzyme are UDP-glucose and gall ...
(UDP-glucose: gallate glucosyltransferase), an enzyme performing the
esterification
In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
of two substrates,
UDP-glucose
Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism.
Functions
UDP-glucose is used in nucleotide sugar metabolism as an activated form of glu ...
and
gallate to yield two products,
UDP and glucogallin. This enzyme can be found in
oak
An oak is a tree or shrub in the genus ''Quercus'' (; Latin "oak tree") of the beech family, Fagaceae. There are approximately 500 extant species of oaks. The common name "oak" also appears in the names of species in related genera, notably ''L ...
leaf preparations.
This the first step in the biosynthesis of
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 ...
s. The molecule is then used by enzymes in the gallotannins synthetics pathway like
beta-glucogallin O-galloyltransferase or
beta-glucogallin-tetrakisgalloylglucose O-galloyltransferase.
β-Glucogallin is
aldose reductase inhibitor Aldose reductase inhibitors are a class of drugs being studied as a way to prevent eye and nerve damage in people with diabetes.
Mechanism
Their target, aldose reductase, is an enzyme that is normally present in many other parts of the body, and ...
.
Half-life of β-Glucogallin in human body seems to be unknown.
References
{{Gallotannin
Gallotannins