TANNINS Ágnes Kéry
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1 TANNINS Ágnes Kéry
2 The original implications of the word tannin clearly indicate a plant material which produces leather from hide. Probably the most acceptable definition is still that of Bate-Smith and Swain, formulated in 1962 (Bate-Smith and Swain, 1962). They adopted the earlier ideas of White (1957) and classified vegetable tannins as water-soluble phenolic compounds having molecular weights between 500/1000 and 3000 and, besides giving the usual phenolic reactions, they have special properties such as the ability to precipitate alkaloids, gelatin and other proteins.
3 Classification of tannins : all tannins are polyphenols but not all polyphenols are tannins molecular mass number of free phenolic groups production of leather form hide
4
5 Tannins are polyphenols: hydrolyzable tannins condensed (not hydrolyzable) tannins Hydrolyzable tannins are esters of sugar (or related polyol) and a variable number of phenolic acid molecules. oxidized when the phenolic acid is gallic acid when the phenolic acid is hexahydroxydiphenic acid or derivatives - gallotannins ellagitannins complex tannins are modified ellagitannins (flavano- and flavano- ellagitannins) Condensed tannins are polymeric flavans. (poranthocyanidins), consisting of flavan-3-ol units. Carbon carbon bonds:
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7 Natural polygalloyl and hexahydroxydiphenoyl esters related biogenetically to ß-penta-O-galloyl-Dglucose (1)
8 Proanthocyanidins
9 Condensed proanthocyanidins
10 Dimeric procyanidins
11 Proanthocyanidin - anthocyanidin polymerisation in red wines
12 Physicochemical properties: - tannins dissolve in water to form colloidal solutions (solubility varies with the degree of polymerization) - like all phenols, they react with ferric chloride heavy metals salts, gelatin make them precipitate out of aqueous solutions - different behavior in acidic medium at high temperature - quantitation methods
13 Biological properties of tannins: Ability to form complexes with macromolecules particularly with proteins. Reversible complexation (in non oxidizing conditions and at physiological ph) - results: formation on the surface of the protein a layer which is less hydrophilic than the protein itself establishing bonds between the protein molecules - affinity is dependent: on the tannin molecular mass it increases with the number of proline residues in the protein it increasis with the flexibility of the protein conformation Irreversible complexation Because of their marked tendency to spontaneously oxidize. (o-quinones react with the nucleophilic groups of proteins to form covalent bonds) The combination becomes irreversible.
14 Polyphenol complexation Protein-polyphenol precipitation
15
16 Chief tannin containing plants Gall Quercus infectoria Olivier (Fagaceae) Cynips (eggs of hymenopterous insects) Witch hazel Hamamelis virginiana L. (Hamammelidaceae) Rhatany Krameria lappacea Burd and Simp. (Krameriaceae) Purple loosestrife Lythrum salicaria L. (Lythraceae) Hawthorn Crataegus monogyna Jacg., Cr. laevigata L. (Rosaceae)
17 Other tannin containing plants Lady s mantle (Alchemilla vulgaris Rothm) Bennet (Geum urbanum L.) Wild strawberry (Fragaria vesca L.) Tormentil (Potentilla erecta Raüsch) Rose (Rosa gallica L.) Blackberry (Rubus fruticosus L.) Bistort (Polygonum bistorta L.) Robert herb (Geranium robertianum L.)
18 Gall Quercus infectoria Olivier (Oak) Fagaceae
19 Quercus robur L. (Oak) Fagaceae
20 Quercus pubescens Willd (Oak) Fagaceae
21 Quercus petraea Liebl (Oak) Fagaceae
22 Hamamelis virginiana L. (Witch Hazel) Hamamelidaceae
23 Krameria triandra Ruiz & Pav. (Rhatany) Krameriaceae
24 Agrimonia eupatoria L. (Agrimony) Rosaceae
25 Alchemilla glabra (= A. vulgaris L.) (Lady s mantle) Rosaceae
26 Geum urbanum L. (Herb benett) Rosaceae
27 Rubus Idaeus L. (Raspberries) Rosaceae
28 Potentilla erecta Rausch (Tormentil) Rosaceae
29 Corylus avellana L. (Hazel) Betulaceae
30 Lythrum salicacia L. (Purple looses trife) Lythraceae
31 Cratageus monogyna Jacg. Rosaceae
32 Crataegus laevigata DC. Rosaceae
33 Vitis vinifera L. (Vine) Vitaceae
34 Acacia catechu Willd (Black catechu) Mimosaceae
35 Industrial sources of tannins Oaks (Quercus sp.) Chestnut tree (Castanea sp.) Acacia (Acacia mearnsii De Willd) Sumac (Rhus typhina L.) Divi divi (Caesalpinia coriara Willd.)
36
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