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TANNINS

Introduction:
Tannins are secondary metabolites, non nitrogenous, phenolic/polyphenous compounds,
present in vacuoles or surface wax or cell sap of the plant that precipitate proteins
(astringent property).
Derived from French word tannin meaning tanning substance
Chemically, mixtures of very diverse group of oligomers and polymers, generally with odihydroxy or o-trihydroxy group on a phenyl ring. (Phenolic class)
Unripe parcemons contains large amount of tannin
Found in

Bud tissues
Seed tissues
Leaf tissues
Stem tissues
Root tissues

Goldbeater skin test:


Confirmatory test to check presence of tannins and differentiate between only true and
pseudo tannins
Piece of goldbeater skin (membrane prepared from intestine of an ox) soaked in 2%HCl.
Ringed with distilled water and placed in a solution of tannin for 5 minutes. Skin is
washed in distilled water and kept in solution of 1% ferrous sulphate solution. A brown
or black color is produced on skin due to presence of tannin.
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Classification of Tannins:

Tannins are classified as:

Pseudotannins:

Occur as gallic acid, catechins, chlorogenic acid, Ipecacuanhic acid


Found in dying tissues and cells

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Ferric chloride test:


a. Hydrolyzable produce blue or black color
b. Non Hydrolyzable produce green color
Hydrolyzable tannins:

Produced by polymerization of simple polyphenols


Present in low amounts in plants
Hydrolyzed to carbohydrate and phenolic acids
Can also by hydrolyzed by hot water, mineral acid (mild acid or base) or enzymes
(tannase)
Hydroxyl groups of these carbohydrates are partially or totally esterified with
phenolic groups
o If gallic acid, then gallotannins.
o If ellagic acid, then ellagitannins
Some are toxic
o Hemorrhagic gastroenteritis
o Necrosis of liver
o Kidney damage with proximal tubule necrosis
Gallic acid is found in clove and rhubarb
Ellagic acid is found in eucalyptus and myrobalans

Gallotannins:

Composed of a core of D-glucose and 6-9 galloyl groups


Tannic acid is major source of gallotannins
o It is penta galloyl-D-glucose core and five more units of galloyl linked to one
of the galloyl of the core
Molecular weight 900

Tannic acid

Ellagitannins:

Molecular weight: 2000-5000


Phenolic group: hexahydroxydiphenic acid
This acid spontaneously dehydrates to the lactone form,
ellagic acid

Non Hydrolysable Tannins:

Resistant to hydrolysis
Also called condensed tannins or Proanthocyanidins or catecholic phenols
More widely distributed
Soluble in water
Found in cinchona, male fern, areca seeds, cherry bark, amla
Chemically oligomers or polymers of flavonoid units linked by C-C bonds which
cannot be cleared by hydrolysis

When treated with acids or enzyme, it polymerizes to insoluble red color


Phlobaphene
o On dry distillation, produce catechol derivatives
Derivatives of flavones like:
o Flavan-3-ol (catechin)
o Flavan-3, 4 diols (Leucoancyanidins)
These phenols are linked to carbohydrate or proteins to produce complex tannin
compounds
Responsible for astringent taste of fruit and wines

Characteristics of tannins:
Colloidal with water
Non crystalline
Soluble in
o Water
o Glycerine
o Alcohol
o Dilute alkalies
o Acetone
Insoluble in
o Organic solvents
Molecular weight: 500 - >20,000

Uses:
Promote healing and formation of new tissues on wound
Treat
o Varicose ulcer
o Hemorrhoids
o Minor burns
o Frostbite
o Gum inflammation

Diarrhea
Intestinal catarrh
Heavy metal poisoning (anti dote)
Nux vomica poisoning (treat by green tea. Contain large amount of tannins;
alkaloids are precipitated)
o AIDS (anti viral activity)
As mordant in dyeing
Manufacture of ink
Sizing paper and silk
Printing fabrics
In manufacture of gallic acid and pyrogallol
In leather industry to convert animal hide into leather
Oak tree containing tannins are used for storing old wine. Tannin leach into it and
give bitter taste
Reagent in analytical chemistry
Green tea contains large amount of tannins. Nux Vomica
o
o
o
o

Some river water is black due to tannins which come from trees nearby as they
leach into water.
Some well water is bitter due to tannins

CRUDE DRUGS CONTAINING TANNINS:


Nutgalls:
Botanical Source:
Pathological outgrowth formed from twigs of Dyers oak tree
Quercus infectoria (Fagaceae)

Collection: Outgrowth caused by puncture of ovum of Cynipis tinctoriae OR Oliver


Adleria galletinctoriae (cynipidae)
Oliver lays eggs on twig in early summer or spring. Grow into larva. Larva pierces the
soft and delicate epidermis of growing point of twig and eggs deposited in there.
Secretion from jaw of larva contain enzyme that stimulate growth of tissue into a
spherical projection. Larva remains in gall and develop into pupa and then to imago
which drills the gall and remains inside for 5-6 months. The fully developed insect flies
but they are collected before insect escape from the gall

Gall is not formed if eggs do not hatch or larva dies

Chemical Constituents: (Hydrolyzable tannins)

50-70% gallotannic acid (official tannic acid)


2-4% gallic acid
Ellagic acid
Syringic acid

Starch

Uses:

Local astringent
Manufacture of ink, dye, and tannic acid
In ointment
In suppository

Hamamelis leaf:
Botanical Source: Obtained from dried leaves of Witch hazel leaves Hamamelis
virginiana (Hamameliaceae)

Chemical Constituents:

Gallotannins
Ellagitannins
Free gallic acid
Proanthocyanidins
Volatile oils (traces, mainly saffrole)

Uses:
Astringent
Treat
o Sprains
o Bruises
o Superficial wounds
o Piles
o Inflammatory swelling
o Diarrhea
o Dysentery
o Mucus discharge
Ingredient of eye lotion
Tonic
Sedative
Valuable in checking external and internal hemorrhage

Pale Catechu/Gambier:
Botanical Source: Dried aqueous extract prepared from leaves and young shoots of
Roxburgh
Uncaria gambier (Rubiaceae)

Collection: Collected first at second year growth when 2 meter in height and then
every year at regular interval of 4-6 months till 15 years. Maximum yield is at 8th year

Material is cut and put into boiling water for 3 hours and stirred well. Leaves and twigs
are taken out and placed on sloping for draining the liquid left. Extract is decanted.
Mark is pressed and washed. Liquid transferred to vessel. Liquid is concentrated till
becomes yellowish-green, thick pasty mass. Cooled till crystallization of catechin.
Cooled semi solid mass is solidified in tray and cut into cubes of uniform size and dried
under sun.

Chemical constituents: (Pseudo tannins)

7-33% catechin
22-25% catechutannic acid
Catechu red
Quercetin
Gambier fluorescin

Uses:

Treat diarrhea
In lozenges
Local astringent
Used in dye
Tanning industries
Technical purpose
Eaten with betel

Black catechu:
Botanical source: Dried aqueous extract prepared from heartwood of Willdenow Acacia
Catechu (Leguminosae)
Collection: Bark and sapwood are stripped from trunk. Chips of heartwood are boiled in
earthen pots with water for decoction. Decoction is filtered and evaporated for
concentrating the filtrate in an iron vessel and color becomes darker due to tannins.
Continuous stirring cause formation of catechin crystals. Evaporation is continued till a
syrupy liquid is obtained. Then spread on leaves of cassia fistula arranged on a wooden
frame and dried for a night. Then cut into pieces.

Chemical Constituents: (Pseudo tannins)

2-12% catechin
25-30% catechutannic acid
4-12% aca-catechin or acacia catechin
Catechu red

Quercetin

Uses:
In medicine as Astringent
Treat
o Throat disease
o Diarrhea
o Mouth trouble
Dyeing
Increase appetite
Calico printing
Tanning industries