Tannins Overview
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Questions and Answers

What is a primary characteristic of hydrolysable tannins?

  • They are referred to as pyrogallol tannins. (correct)
  • They produce a green color with ferric chloride.
  • They are insoluble in water.
  • They contain primarily flavonoids.
  • Which term is alternatively used for condensed tannins?

  • Polyphenolic tannins
  • Hydrolysable tannins
  • Gallic tannins
  • Proanthocyanidins (correct)
  • What color do condensed tannins produce when tested with ferric chloride?

  • Red
  • Green (correct)
  • Blue
  • Yellow
  • What product is formed when condensed tannins are treated with acids or enzymes?

    <p>Phlobaphens (B)</p> Signup and view all the answers

    Which families of plants are known to be rich in both hydrolysable and condensed tannins?

    <p>Rosaceae and Geraniaceae (A)</p> Signup and view all the answers

    What are pseudotannins characterized by?

    <p>Simple phenolic compounds of lower molecular weight. (D)</p> Signup and view all the answers

    What is one of the protective functions of tannins in plants?

    <p>Exerting an inhibitory effect on enzymes (B)</p> Signup and view all the answers

    Which of the following is NOT a characteristic of tannins?

    <p>Crystalline substance (D)</p> Signup and view all the answers

    What distinguishes true tannins from pseudotannins in the context of the Goldbeater’s skin test?

    <p>True tannins yield a positive testing result. (A)</p> Signup and view all the answers

    Which of the following best describes hydrolysable tannins?

    <p>Their structure includes molecules of polyphenolic acids linked to glucose. (B)</p> Signup and view all the answers

    How are gallotannins classified under hydrolysable tannins?

    <p>They involve gallic acid in their structure. (C)</p> Signup and view all the answers

    What is the role of the mineral acids in the classification of tannins?

    <p>They help to hydrolyze tannins for further classification. (A)</p> Signup and view all the answers

    Which of the following statements correctly describes condensed tannins?

    <p>They are not affected by hydrolysis. (C)</p> Signup and view all the answers

    What is one characteristic of high molecular weight compounds typically associated with true tannins?

    <p>They are generated from the polymerization of simple phenols. (D)</p> Signup and view all the answers

    Which of these acids is not mentioned as a component of hydrolysable tannins?

    <p>Flavonoid acid (B)</p> Signup and view all the answers

    Which process can help to categorize tannins based on their structure?

    <p>Hydrolytic reaction with enzymes. (A)</p> Signup and view all the answers

    What does a positive Goldbeater's skin test indicate?

    <p>Presence of tannins (C)</p> Signup and view all the answers

    Which test involves the use of sodium acid phosphate and phenazone to detect tannins?

    <p>Phenazone test (B)</p> Signup and view all the answers

    In the gelatin test, what causes the precipitation of gelatin?

    <p>Presence of tannins (B)</p> Signup and view all the answers

    The Matchstick Test detects catechin by indicating the presence of which compound?

    <p>Phloroglucinol (A)</p> Signup and view all the answers

    Which plant sources are known to contain significant amounts of tannins?

    <p>Oak bark and hamamelis leaves (C)</p> Signup and view all the answers

    What color change indicates the presence of chlorogenic acid in a sample?

    <p>Green (A)</p> Signup and view all the answers

    What forms as a result of the Vanillin-hydrochloric acid test when tannins are present?

    <p>Red or pink color (C)</p> Signup and view all the answers

    Which of the following statements about pseudotannins is accurate?

    <p>They show very little color change in tests. (C)</p> Signup and view all the answers

    In which regions is U.gambier primarily cultivated?

    <p>Indonesia, Malaysia, Singapore (B)</p> Signup and view all the answers

    What is the maximum yield of U.gambier typically obtained?

    <p>During the eighth year of growth (A)</p> Signup and view all the answers

    What is the primary method of propagation for U.gambier?

    <p>Seeds (B)</p> Signup and view all the answers

    What temperature is used for boiling the leaves and twigs of U.gambier during processing?

    <p>Boiling water (D)</p> Signup and view all the answers

    Which component constitutes over 60% of the drug derived from U.gambier?

    <p>Phlobatannin catechutannic acid (B)</p> Signup and view all the answers

    What percentage of indole alkaloid can be found in U.gambier?

    <p>Up to 0.05% (A)</p> Signup and view all the answers

    What is the final state of the extract after the drying process?

    <p>Cubes (B)</p> Signup and view all the answers

    Which of the following components is associated with fluorescence under UV light in U.gambier?

    <p>Gambirtannin (B)</p> Signup and view all the answers

    Which solvents are tannins soluble in?

    <p>Alcohol and dilute alkali (D)</p> Signup and view all the answers

    What do tannins form when they bind with proteins?

    <p>Insoluble or soluble tannin-protein complexes (D)</p> Signup and view all the answers

    What is the molecular weight range of tannins?

    <p>500 to &gt;20,000 (B)</p> Signup and view all the answers

    Which structure is tannins vastly known to contain?

    <p>Polyphenols (C)</p> Signup and view all the answers

    What is a pharmacological activity associated with tannins?

    <p>Astringent (C)</p> Signup and view all the answers

    Which of the following phenolic compounds is involved in the formation of tannins?

    <p>Gallic acid and flavan-3,4-diol (A)</p> Signup and view all the answers

    Which statement is true about hydrolysable and condensed tannins?

    <p>Both are soluble in water and alcohol (C)</p> Signup and view all the answers

    Which of the following is NOT a test for the presence of tannins?

    <p>Ninhydrine Test (D)</p> Signup and view all the answers

    What enzyme is capable of hydrolyzing tannins?

    <p>Tannase (D)</p> Signup and view all the answers

    How are proanthocyanidins (PAs) formed?

    <p>By autoxidation of leucocyanidins (D)</p> Signup and view all the answers

    What is a common method for the extraction of tannic acid?

    <p>Water-saturated ether or a mixture of water, alcohol, and ether (D)</p> Signup and view all the answers

    Hydrolysable tannins are also known as what?

    <p>Phlobatannins (D)</p> Signup and view all the answers

    Which term is NOT synonymous with Condensed Tannins?

    <p>Non-Hydrolysable tannins (C)</p> Signup and view all the answers

    A Flavan-3-ol condensed tannin is commonly referred to as?

    <p>Catechin (D)</p> Signup and view all the answers

    What characteristic does NOT typically apply to tannins?

    <p>Soluble with acetone (B)</p> Signup and view all the answers

    Flashcards

    What are polyphenols?

    Compounds containing multiple phenol groups, responsible for astringent properties. They're found in plants and are often used in food, beverages, and medicine.

    What is Goldbeater's Skin Test?

    A test used to classify tannins. True tannins react positively, forming a precipitate with hide powder. Pseudotannins react weakly or not at all.

    What are True tannins?

    Large, complex molecules made of many smaller phenol units. These are responsible for the characteristic astringent properties often associated with tannins.

    What are Pseudotannins?

    Tannins that do not react strongly in the Goldbeater's Skin Test. They are less effective at tanning.

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    What are Hydrolysable tannins?

    These tannins can be broken down (hydrolyzed) by acids or enzymes. They are made up of smaller polyphenolic acids connected to a central sugar molecule.

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    What are Condensed tannins?

    These tannins cannot be broken down (hydrolyzed) by acids or enzymes. Instead, they are formed by the joining of smaller phenol units.

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    What are Gallotannins?

    A type of hydrolysable tannin formed from gallic acid units. These are commonly found in plants like gallnuts, tea, and oak bark.

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    What are Ellagitannins?

    A type of hydrolysable tannin formed from hexahydrodiphenic acid units. They are often found in fruits like blueberries, raspberries, and strawberries.

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    Hydrolysable Tannins

    Tannins that can be broken down into simpler molecules by hydrolysis, which release phenolic acids like pyrogallol upon dry distillation. They are soluble in water and form a blue color with ferric chloride.

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    Condensed Tannins

    Tannins that are not easily hydrolyzed into smaller components, also known as nonhydrolysable tannins. They are related to flavonoids in their structure and often linked to carbs or proteins. They produce red phlobaphens when treated with acids or enzymes.

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    Catechin

    A structural component of condensed tannins, a flavan-3-ol that contributes to their properties.

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    Leucoanthocyanidins

    Another structural component of condensed tannins, a flavan-3,4-diol that often becomes part of the tannin structure.

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    Phlobaphens

    Insoluble red products formed from condensed tannins when they are treated with acids or enzymes. They contribute to the red color of certain medicines like cinchona bark.

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    Pseudotannins

    Simple phenolic compounds with lower molecular weights than regular tannins. They don't exhibit the same tanning properties as regular tannins.

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    Gallic Acid

    A well-known pseudotannin found in many plants, a simple phenolic acid.

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    Chlorogenic Acid

    A specific type of pseudotannin that is common in plants, particularly in dead or dying cells.

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    Tannins

    A class of secondary metabolites that impact animal nutrition, known for their ability to bind with proteins and form complexes, and are commonly found in plants.

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    Tannin Solubility

    Tannins are soluble in water, alcohol, dilute alkali, and glycerin. They are sparingly soluble in ethyl acetate.

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    Tannins Solubility (Organic)

    Tannins are insoluble in most organic solvents except acetone.

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    Tannin Structure

    Tannins are oligomeric compounds, meaning they are made up of multiple smaller units linked together. These units are usually derived from phenolic compounds and have free phenolic groups.

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    Tannin Molecular Weight

    Tannins can range in molecular weight from 500 to over 20,000. This wide range depends on the number of phenolic units linked together in the molecule.

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    Tannin Formation

    Common tannins are often formed from gallic acid and ellagic acid. These acids undergo oxidative coupling to create larger tannin polymers.

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    Goldbeater's Skin Test

    A test that uses goldbeater's skin (a membrane from an ox's intestine) to detect the presence of tannins.

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    Phenazone Test

    A test that uses phenazone solution to precipitate tannins from an aqueous solution.

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    Gelatin Test

    A test that uses gelatin solution to precipitate tannins.

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    Matchstick Test (for Catechin)

    A test that uses a matchstick (containing lignin) to detect catechin, which reacts with hydrochloric acid to produce phloroglucinol, staining the wood pink or red.

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    Test for Chlorogenic Acid

    A test that uses ammonia to detect chlorogenic acid, which turns green when exposed to air.

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    Vanillin-Hydrochloric Acid Test

    A test that uses vanillin and hydrochloric acid to produce phloroglucinol, which reacts with vanillin to give a pink or red color.

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    What are tannins?

    Complex molecules found in plants that have astringent properties.

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    Examples of Plants with Tannins

    Plants containing tannins as their major active constituents, such as oak bark, hamamelis leaves, and bearberry leaves.

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    What is the pharmacological activity of tannins?

    Tannins are known to have an astringent pharmacological activity, which causes a tightening sensation.

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    What test is used to detect the presence of tannins?

    The Gold Beater's Test is used to detect the presence of tannins by observing the formation of a precipitate with hide powder.

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    What enzyme hydrolyzes tannins?

    The enzyme tannase is responsible for breaking down tannins into smaller molecules.

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    What is another name for a flavan-3-ol condensed tannin?

    A flavan-3-ol condensed tannin is also known as a catechin, a type of molecule found in plants.

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    List the characteristics of tannins.

    Tannins are known for forming solutions with water and binding to proteins. However, they are non-crystalline substances and are not always soluble in acetone.

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    What is the primary use of Uncaria gambier?

    The plant Uncaria gambier is primarily grown for the pharmaceutically active drug it produces, which is mainly traded through Singapore.

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    How does cultivation of Uncaria gambier start?

    The cultivation of Uncaria gambier involves sowing seeds in a nursery, allowing seedlings to grow for about nine months before transplanting them into open areas with spacing of approximately 3 meters.

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    When is the first harvest of Uncaria gambier?

    The first harvest from Uncaria gambier is collected during the second year of growth, and involves gathering leaves and young shoots. Subsequent harvests occur annually.

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    What is the optimal yield period for Uncaria gambier?

    While Uncaria gambier can produce leaves and twigs for up to 20 years, optimal yields are achieved during the eighth year of its growth cycle.

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    How are cubes of Uncaria gambier extract produced?

    Cubes are produced by cooling and solidifying the concentrated extract, then cutting it into shape. The process involves boiling, draining, pressing, concentrating, and shaping in wooden trays.

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    What are the key constituents of Uncaria gambier extract?

    Pale catechu, the extract of Uncaria gambier, contains two primary constituents: catechin, a pseudotannin, and catechutannic acid, a phlobatannin. These two make up over 60% of the extract.

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    Besides the two main components, what else does Uncaria gambier extract contain?

    Pale catechu also contains additional compounds such as catechu red, gambier fluorescin, and quercetin. Additionally, it has a small amount of indole alkaloids, including gambirtannin and its derivatives.

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    What property does gambirtannin, an alkaloid found in Uncaria gambier extract, have?

    Gambirtannin, an indole alkaloid in pale catechu, displays a strong fluorescence under UV light.

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    Study Notes

    Tannins

    • Tannins are complex organic plant compounds with astringent properties, derived from the French word "tanin"
    • They are widespread in the plant kingdom
    • Early use of tannins was for tanning animal hides to leather (tanning)
    • Tannins combine with animal hides through a test called Goldbeater's skin test
    • Two major groups of tannins:
      • Hydrolysable tannins: Hydrolyzed by minerals/enzymes, contain phenolic acids (gallic/ellagic) linked to a central glucose molecule
        • The phenolic acids are important to their further classification
        • Soluble in water; blue color with ferric chloride
      • Condensed tannins (proanthocyanidins): Not readily hydrolyzed; contain only phenolic nuclei related to flavonoids
        • Catechin and leucoanthocyanidins are examples of the phenolic compound in condensed tannins
        • Produce insoluble red coloured products (phlobaphens) when treated with acids/enzymes
        • Soluble in water but produce green color with ferric chloride

    Pseudotannins

    • Simple phenolic compounds with low molecular weight, do not react in the Goldbeater's skin test
    • Examples include gallic acid, chlorogenic acid, and catechin

    Tannin Characteristics

    • Colloidal solutions in water (some high MW exceptions)
    • Insoluble in organic solvents (except acetone)
    • Soluble in alcohols, dilute alkali, and glycerin

    Crude Drugs Containing Tannins

    • Nutgalls from the plant Quercus infectoria: A pathological outgrowth on twigs of oak tree; important source for tannic acid (gallotannic acid)
      • Collected in Turkey, Syria, etc.
    • Pale Catechu (Gambier): Dried water extract of leaves and twigs of Uncaria gambier tree (Rubiaceae family)
      • Native to Southeast Asia
    • Black Catechu (Cutch): Dried extract of the heartwood of Acacia catechu:
      • (Leguminosae family), distributed throughout India
    • Other plants are known to contain tannins, including parts of some fruits and leaves

    Tannin Uses

    • Tanning leather
    • Dyeing materials (e.g., fabrics)
    • Pharmaceuticals (as astringents)
    • Manufacturing inks, sizing paper, and similar products
    • Various other uses including medicine & clarification of beer/wine
    • Can bind to proteins, forming soluble or insoluble tannin-protein complexes

    Additional Tests

    • Goldbeater's skin test: Identifies true tannins by their ability to tan the membrane
    • Phenazone test, Gelatin Test, Catechin test (Matchstick Test) & Vanillin-hydrochloric acid test
      can be used to further ascertain the presence of different types of tannins

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    Description

    Explore the fascinating world of tannins, complex organic compounds found in plants. Learn about their astringent properties, major groups, and significance in processes like tanning animal hides. This quiz delves into hydrolysable and condensed tannins, highlighting their chemical structures and reactions.

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