tannins Flashcards
this term was first applied by Seguin in 1796 to denote substances present in plant extracts which were able to combine with protein of animal hides, prevent their putrefaction and convert them into leather.
TANNINS
Tannins Is a substance which is detected qualitatively by ___
Tannin Test (Goldbeater’s Skin Test)
Tannins Is a substance which is determined quantitatively by its
absorption on standard hide powder.
T OR F
Only a few tannins are glycosides
FALSE
Tannins are source of fruit acids. Enumerate.
Glycolic
Lactic
Mandelic
Malic
Tartaric
Citric acid
T OR F
Tannins are found in mature fruits.
False
Tannins are found in specific plant parts. Enumerate.
Leaves
Fruits
Barks
Stems
Are Found in great quantities in dead or drying cells.
Occur in solution in cell sap, often in distinct vacuoles.
Tannins
a mixture of polyphenols and non-crystallizable compounds
Complex Substance
This may be hydrolyzed by acids or enzymes such as Tannase.
Hydrolysable Tannins
Hydrolysable Tannins may be hydrolyzed by acids or enzymes such as ____.
Tannase
They form several molecules of phenolic acids as Gallic acid and Hexahydroxy-diphenic acid which are united by ester linkages to a central glucose molecules.
Hydrolysable Tannins
What are hydrolysable tannins formerly known as?
Pyrogallol Tannins
dry distillation, Gallic acid and similar components are converted to
Pyrogallol
Hydrolysable Tannins When treated with acids/enzymes
Phenolic Acids (Gallic Acid, Ellagic Acid, Glucose)
Gallitannins
Gallic Acid
Ellagitannins
Hexahydroxy-diphenic acid units
Ferric Chloride (Hydrolysable Tannins)
Blue Color
Bromides (Hydrolysable Tannins)
No precipitate
Condensed Tannins (Proanthocyanidins, Polyflavonoid, Catechol-type, Pyrocatecollic-type tannins)
Non-Hydrolysable Tannins
Are not readily hydrolyzed to simpler molecules and they do not contain a sugar moiety.
Non-Hydrolysable Tannins
Are related to the Flavonoid pigments and have polymeric Flavan-3-ol structures.
Non-Hydrolysable Tannins
Catechins which also occur with the tannins and Flavan in the biosynthesis of the molecules.
Non-Hydrolysable Tannins
Non-Hydrolysable Tannins When treated with acids/enzymes
converted into red insoluble compounds known as Phlobaphenes
It gives the characteristic color to many drugs (red cinchona bark)
Phlobaphenes
Non-Hydrolysable Tannins when subjected to dry distillation
Catechols called as Catechol Tannins
Ferric Chloride (Non-Hydrolysable Tannins)
Greenish
Bromides (Non-Hydrolysable Tannins)
Precipitate
Are compounds of lower molecular weight than true tannins and they do not respond to the Goldbeater’s skin test
Pseudotannins
Pseudotannins are Formed by either linkages between two or more molecules of Phenolic acid:
Digallic and Chlorogenic Acid
Pseudotannins And others are derivatives of Flavan
Catechins/Catechols
Pseudotannins
Example - Gallic Acid:
Rhubarb and most materials which contains gallitannins
Pseudotannins
Examples - Catechins:
Catechu, Acacia cutch, Kino, Cocoa, Guarana
Pseudotannins
Examples - Chlorogenic acid:
Unroasted coffee, Nux vomica
Pseudotannins
Examples - Ipecacuanha acid:
Ipecacuanha
Pyrocatechol/Phlobatannins
▪Heated -
Catechol
Pyrocatechol/Phlobatannins
▪Boiled with HCl -
Insoluble Red Phlobaphenes
Pyrocatechol/Phlobatannins
Treated with FeCl3 T.S. -
Green Color
Pyrocatechol/Phlobatannins
▪Treated with Bromine T.S. -
Formed Precipitate
Pyrocatechol/Phlobatannins Examples
Kino
Gambir
Pyrogallol Tannins
▪ Heated
Pyrogallol
Pyrogallol Tannins
▪ Boiled with HCl -
Gallic Acid/Ellagic Acid
Pyrogallol Tannins
▪ Treated with FeCl3 T.S. -
Blue Color
Pyrogallol Tannins
▪ Treated with Bromine T.S.
No Precipitate
Pyrogallol Tannins Examples
Nut gall
Oak Bark
Pomegranate Bark
Tannins Uses
- Antiseptic
❑ Astringent
❑ Antidote for Alkaloidal poisoning
❑ Preservative on leather
❑ Laboratory reagent for protein and alkaloid identification.
❑ Ink industries
Antioxidants
- Leucoanthocyanidins
▪ Proanthocyanidins
▪ Pycnogenol
Improves peripheral circulation, capillary fragility, retinophaties, inflammatory collagen disease
Grape Seeds - Vitis vinifera
Needles and Barks of Pine Tree - Pinus pinaster
Tests for Tannins
- Solubility
❑ Reaction with Ferric Salts
❑ Goldbeater’s Skin Test
❑ Phenazone Test
❑ Gelatin Test
❑ Test for Catechin
❑ Test for Chlorogenic Acid
Plants with Rich Sources of Tannins in Flowers
Lime
Hawthorn
Plants with Rich Sources of Tannins in Fruits
Cranberry
Grapes
Hawthorn
Plants with Rich Sources of Tannins in Seeds
Areca
Cacao
Guarana
Kola
Plants with Rich Sources of Tannins in Leaves
Hamamelis
Hawthorn
Plants with Rich Sources of Tannins in Barks
Acacia
Cinnamon
Hamamelis
Oak
Willow
Wild Cherry
Plants with Rich Sources of Tannins in Roots and Rizomes
Krameria
Male Fern
Plants with Rich Sources of Tannins in Extracts and Dried Juices
Butea Gum
Acacia Catechu
Mangrove
East Indian Kino
Eucalyptus Kino
High rates of oral esophageal cancer in India and South Africa.
Habitual Chewing of Betel Nut
Lower incidence of esophageal cancer in British than Dutch.
Drinking of Ordinary Tea
TANNIN-RICH PLANT FAMILIES
❑ Combretaceae - Quisqualis
❑ Geraniaceae - Geraniums
❑ Leguminosae – Acacia, Tamarind
❑ Myrtaceae – Eucalyptus, Guava
❑ Polygonaceae – Buckwheat
❑ Rosaceae – Red rose
❑ Rubiaceae – Gambir
❑ Theaceae – Tea
❑ Plant polyphenols
❑ “Tannin Extracts”
❑ Non-crystallizable
Tannins
❑ Precipitate proteins
❑ Sharp “puckering” taste
Tannins