Tannin

Lia Marliani, M.Si., Apt.

Biologi Farmasi, Sekolah Tinggi Farmasi Bandung
 Tannins comprise a group of compounds with a wide diversity in structure
that share their ability to bind and precipitate proteins. The name tannins
refers to the process of tanning animal skin to form leather

Tannins
 Adstringent

binds to and precipitates proteins and various other organic compounds

Tannins including amino acids and alkaloids

molecular weights ranging from 500 to over 3,000 (gallic acid esters)
and up to 20,000 (proanthocyanidins)
  Tannins are freely soluble in water, alcohol, glycerol, and
acetone and dilute alkalies. They are sparingly soluble in
chloroform, ethyl acetate and other organic solvents.
 They have an astringent taste.
 They yield purple, violet or black precipitate with iron
Properties compounds. They are precipitated by number of metallic
salts notably potassium dichromate, and lead acetate and
sub acetate.
 They combine with skin and hide to form leather and with
gelatin and isinglass to form an insoluble compound. They
combine with alkaloids to form tannates, most of which are
insoluble in water.
Condensed tannins are also referred
to as proanthocyanidins. They are
oligomeric or polymeric flavonoids
consisting of flavan-3-ol (catechin)
units. Hydrolysis under harsh
conditions, such as heating in acid,
yields anthocyanidins. An example of
a condensed tannin is procyanidin B 2

(epicatechin-(4β→8′)-epicatechin;
1.90)
Gallotannins are hydrolysable tannins with a polyol core (referring to a compound with multiple hydroxyl
groups) substituted with 10-12 gallic acid residues. Gallotannins contain the characteristic meta-depside
bonds (1.91) between gallic acid residues. This bond is more labile than an aliphatic ester bond, and can
be methanolyzed with a weak acid in methanol. In contrast, methanolysis of an aliphatic ester bond
requires methanol with a strong mineral acid and heat. 6-pentagalloylglucose (1,2,3,4,6-penta-O-galloyl-
β-D-glucopyranose; 1.92; An example of a gallotannin is the hexagalloylated compound 2-O-digalloyl-
1,3,4,6-tetra-O-galloyl-β-D-glucopyranose (1.93)
Ellagitannins are also hydrolysable tannins
derived from pentagalloylglucose (1.92), but
unlike gallotannins, they contain additional C-C
bonds between adjacent galloyl moieties in the
pentagalloylglucose molecule. This C-C linkage is
formed through oxidative coupling between the
two adjacent galloyl residues, and results in the
formation of a hexahydroxydiphenoyl (HHDP)
unit, which can have either the S- (1.94) or the R-
configuration (1.95)
The name ellagitannins is derived from ellagic
acid (1.96), which is formed spontaneously from
hexahydroxydiphenic acid (1.94/1.95) in aqueous
solution via an intra-molecular esterification
reaction
Complex tannins are defined as tannins in
which a catechin unit is bound glycosidically to
either a gallotannin or an ellagitannin unit. As
the name implies, the structure of these
compounds can be very complex. An example
is Acutissimin A (1.99)
Biosynthesis
Biosynthesis
The shikimate pathway
provides an alternative route
to aromatic compounds,
particularly the aromatic
amino acids l-phenylalanine,
l-tyrosine, and l-tryptophan
  Biosintesis tanin
katekat merujuk
kepada
BiosintesisTanin biosintesis
katekin
(flavonoid)
Gallotannins
Gallotannins
Sumber
Tanin
Sumber
Tanin
 Antibacterial

Tannins Adstringent
Acti Antioxidant
vity

Anticarcinogenic

Tannins form complexes with proteins, starch, and digestive enzymes

Anticancer
  In guava leaves, comparison for solvent extraction for
tannins by using ethanol and acetone which resulted
that ethanol 30% (v/v) is the best solvent
 Tannins also extracted from the bark of Pinus oocarpa
with sodium carbonate and sodium bisulfite
Extraction  Tannins of Galium tunetanum were extracted by two
methods by ethanol 30% for 2 hours and the other by
acetone for 24 hours
 Extraction of three Acacia species using distilled water,
80% methanol and 70% acetone, showed that the 70%
acetone was the most efficient solvent among the
three solvent used
  Like all phenols, tannins react with ferric salts. Gallotannins and
ellagitannins with ferric salts give bluish-black colour and
precipitates, but condensed tannins cause greenish-brown
precipitates (at the presence of formic aldehyde and
hydrochloric acid).
 Tannins cause precipitation of gelatin solution.
Identification  Tannins precipitate with solutions of alkaloids.
 Treated with lead acetate (Pb 2+) in the acidic medium,
hydrolyzable tannins precipitate, condensed remain in the
aqueous layer.
 Chromatography is used for detection of only low-molecular-
weight tannins.
 Bioactivity and mechanism
Task
Purification and
Identification
  Per group
a. Paper : A4, top margin 1,2 inch; bottom
margin 0,8 inch; left margin 1,1 inch; right
margin 0,8 inch
Task b. Font Calibri 11pt; spasi 1,5; no before or
after; indent new paragraph left 0.5”
c. Refferences : journal, Harvard style