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    Alkaloids

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    SajanMaharjan
    Alkaloids are nitrogen-containing organic compounds derived from plants that are physiologically active. While they are typically basic and derived from amino acids, some alkaloids deviate from this definition by not being basic, containing nitrogen outside of a heterocyclic ring, or being derived from sources other than plants. Common alkaloids include morphine, codeine, quinine, and caffeine. They can be classified based on their biosynthetic pathway, with major classes including isoquinoline, indole, quinoline, and tropane alkaloids. Qualitative chemical tests can identify alkaloids based on precipitation reactions. Physically, alkaloids vary in properties like state, color, and solubility

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    Alkaloids

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    SajanMaharjan
    356 views36 pages
    Alkaloids are nitrogen-containing organic compounds derived from plants that are physiologically active. While they are typically basic and derived from amino acids, some alkaloids deviate from this definition by not being basic, containing nitrogen outside of a heterocyclic ring, or being derived from sources other than plants. Common alkaloids include morphine, codeine, quinine, and caffeine. They can be classified based on their biosynthetic pathway, with major classes including isoquinoline, indole, quinoline, and tropane alkaloids. Qualitative chemical tests can identify alkaloids based on precipitation reactions. Physically, alkaloids vary in properties like state, color, and solubility

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    Alkaloids are nitrogen-containing organic compounds derived from plants that are physiologically active. While they are typically basic and derived from amino acids, some alkaloids deviate from this definition by not being basic, containing nitrogen outside of a heterocyclic ring, or being derived from sources other than plants. Common alkaloids include morphine, codeine, quinine, and caffeine. They can be classified based on their biosynthetic pathway, with major classes including isoquinoline, indole, quinoline, and tropane alkaloids. Qualitative chemical tests can identify alkaloids based on precipitation reactions. Physically, alkaloids vary in properties like state, color, and solubility

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    356 views36 pages

    Alkaloids

    Uploaded by

    SajanMaharjan
    Alkaloids are nitrogen-containing organic compounds derived from plants that are physiologically active. While they are typically basic and derived from amino acids, some alkaloids deviate from this definition by not being basic, containing nitrogen outside of a heterocyclic ring, or being derived from sources other than plants. Common alkaloids include morphine, codeine, quinine, and caffeine. They can be classified based on their biosynthetic pathway, with major classes including isoquinoline, indole, quinoline, and tropane alkaloids. Qualitative chemical tests can identify alkaloids based on precipitation reactions. Physically, alkaloids vary in properties like state, color, and solubility

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    © All Rights Reserved
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    of 36

    ALKALOIDS

    Alkaloids
    Definition: the term alkaloid (alkali-like) is commonly used
    to designate basic heterocyclic nitrogenous compounds of plant
    origin that are physiologically active.
    Derived from amino acids.

    DEVIATION FROM DEFINITION:


    Basicity: Some alkaloids are not basic e.g. Colchicine,
    Piperine, Quaternary alkaloids.
    Nitrogen: The nitrogen in some alkaloids is not in a
    heterocyclic ring e.g. Ephedrine, Colchicine, Mescaline.
    Plant Origin: Some alkaloids are derived from Bacteria,
    Fungi, Insects, Frogs, Animals.
    Biosynthesis: Some alkaloids are not derived from amino
    acids e.g purine, steroidal alkaloid .

    QUALITATIVE CHEMICAL TESTS FOR ALKALOIDS


    General tests answered by all alkaloids are as follows:
    1. Dragendorffs test: To 23 mL of the alkaloid solution add few drops of
    Dragendorffs reagent (potassium bismuth iodide solution). An orange brown
    precipitate is formed.
    2. Mayers test: To 23 mL of the alkaloid solution add few drops of Mayers
    reagent (potassium mercuric iodide solution). White brown precipitate is
    formed.
    3. Hagers test: To 23 mL of the alkaloid solution add few drops of Hagers
    reagent (saturated solution of picric acid). Yellow precipitate is formed.
    4. Wagners test: To 23 mL of the alkaloid solution add few drops of Wagners
    reagent (iodine potassium iodide solution). Reddish brown precipitate is
    formed.

    Physical Properties:
    I- State:

    Most alkaloids are crystalline solids.

    Few alkaloids are amorphous solids e.g. emetine.

    Some are liquids that are either:


    Volatile e.g. nicotine and coniine, or
    Non-volatile e.g. pilocarpine and hyoscine.

    II- Color:
    The majority of alkaloids are colorless but some are colored e.g.:

    Colchicine and berberine are yellow.

    betanidine is orange.

    The salts of sanguinarine are copper-red.

    III- Solubility:

    Both alkaloidal bases and their salts are soluble in alcohol.

    Generally, the bases are soluble in organic solvents and insoluble in water
    Exceptions:
    Bases soluble in water: caffeine, ephedrine, codeine, colchicine, pilocarpine
    and quaternary ammonium bases.
    Bases insoluble or sparingly soluble in certain organic solvents: morphine
    in ether, theobromine and theophylline in benzene.

    Salts are usually soluble in water and, insoluble or sparingly soluble in organic
    solvents.
    Exceptions:
    Salts insoluble in water: quinine monosulphate.
    Salts soluble in organic solvents: lobeline and apoatropine hydrochlorides are
    soluble in chloroform

    Chemical Properties
    Most of the alkaloids are basic in nature, due to the availability of lone pair of electrons on
    nitrogen.
    The basic character of the alkaloid compound is enhanced if the adjacent functional groups
    are electron releasing.
    The alkaloid turns to be neutral or acidic when the adjacent functional groups are electron
    withdrawing like amide group which reduces the availability of the lone pair of electron.
    Their salt formation with an inorganic acid prevents many a time their decomposition.
    In the natural form, the alkaloids exist either in Free State, as amine or as salt with acid or
    alkaloid N-oxides.
    The alkaloid may contain one or more nitrogen and exist in the form of
    Primary amines

    R-NH2

    e.g. Norephedrine

    Secondary amines

    R2-NH

    e.g. Ephedrine

    Tertiary amines

    R3-N

    e.g. Atropine

    Quaternary ammonium salts R4-N e.g

    d-Tubocurarine

    Biosynthetic classification
    1. Ornithine derived alkaloids
    e.g. Pyrrolidine alkaloid-nicotine
    Tropane alkaloid Atropine, hyosyamine, coacaine
    2. Lysine derived alkaloids
    e.g. Piperidine and pyridine alkaloid conine, lobaline, arecoline
    Quinazolidine alkaloid- lupinine
    3. Tyrosine derived alkaloids
    e.g. Isoquinoline alkaloid morphine, codeine, emetine, cephaline, berberine, d- tubocurine
    Amino alkaloid- colchicine
    4. Tryptophan derived alkaloids
    e.g. Indole alkaloid- ergot alkaloid, vincristine, vinblastine, reserpine, strychnine,
    physostigmine, strychinine, brucine
    Quinoline alkaloid cinchonine, quinine, quinidine, camptothecin
    5. Histidine derived alkaloids
    e.g. Imidazole alkaloid Pilocrpine
    6. Phenylalanine derived alkaloids
    e.g. Amino alkaloid- Ephedrine

    General reactions for biosynthesis of alkaloids


    Some of the general reactions that are of particular

    importance

    include:

    decarboxylation

    (removal

    of

    carboxyl group or carbon dioxide) and transamination


    (transfer of an amino group from one molecule to
    another without

    the formation of ammonia) of the

    amino

    yield

    acids

    to

    corresponding

    amine

    or

    aldehyde.
    These can react to form a Schiff base which, in turn can

    react with carbanion in a Mannich-type condensation.

    Alkaloid formation may require the involvement


    of only one molecule of amino acid, or 2
    molecules of the same AA, or less commonly, 2
    molecules of different AA or else several
    molecules of the same AA.

    General reaction

    ORNITHINE DERIVED ALKALOIDS


    It includes:

    Tropane alkaloids

    Pyrrolidine alkaloids`

    TROPANE ALKALOIDS
    (ATROPINE, HYOCYAMINE, HYOSINE, SCOPOLAMINE)

    B.S: Atropa belladona (deadly nightshade), Datura


    stramonium( thornapple), Hyosyamus niger(henbane).
    Family: solanaceae
    Part used: dried leaves and flowering tops
    Uses: 1.Atropine is classified as anti cholinergic drugs.
    Atropine can also be used in SLUDGE syndrome( salivation,
    lacrimation, urination, diaphoresis, GIT motility and emesis)
    caused by organophosphate poisoning.
    Hyoscine is used as antispasmodic.

    TRYPTOPHAN DERIVED ALKALOIDS

    These include
    INDOLE ALKALOIDS
    QUINOLINE ALKALOIDS

    QUINOLINE ALKALOIDS
    The alkaloids containing essentially the quinoline nucleus
    include a series of alkaloids obtained exclusively from
    the cinchona bark, the major members of this particular group
    are, namely: quinine, quinidine, cinchonine and cinchonidine.
    Basic Structures

    Properties
    Quinine is very slightly soluble in H2O, soluble in ethanol,
    chloroform, ether, benzene and other organic solvents.
    Quinine is a diacidic base. It forms 2 types of sulfates:
    Quinine sulfate (neutral and H2O insoluble).
    Quinine bisulfate (acidic and H2O soluble).
    Quinine (l-isomer) gives quinidine (d-isomer) among other
    products when warmed with KOH in amyl alcohol.
    Quinine is levorotatory, while quinidine is dextrorotatory.
    Tartrates of Quinine and Cinchonidine are insoluble, whereas
    the tartrates of Cinchonine and Quinidine are soluble in water.

    Tests for identification


    1- Fluorescence test:
    Solution of the alkaloid in oxygenated acids (e.g H 2SO4, HNO3 or
    phosphoric acid) blue fluorescence (+ ve with quinine and quinidine).
    2- Thalleoquine test:
    Aqueous solution of the alkaloidal salt + Br 2 /H2O (few drops till the
    appearance of yellow color) + NH4OH emerald green color
    (+ ve with quinine and quinidine).
    3- Rosequin test (Erythroquinine test):
    Aqueous solution of the alkaloidal salt + dil HCl + Br 2 /H2O (few drops till
    the
    appearance of yellow color) + CHCl 3 + pot. Ferrocyanide +
    NH4OH
    red color in the CHCl3 layer (+ ve with quinine and quinidine).

    Uses
    Quinine is used mainly as anti-malarial in a dose of 2g of
    quinine sulfate or other salt for 14 days.
    Quinidine is used as a cardiac depressant (antiarrhythmic), particularly to inhibit auricular fibrillation in
    a dose of 0.6-1.6 g of quinidine sulfate daily.
    Cinchonine and cinchonidine are used as antiinflammatory.
    Quinine is used as a flavor in carbonated beverages.

    Indole alkaloids
    Physostigma alkaloids

    Botanical source. Physostigma


    venonosum
    Common name: calabar bean
    Family : Leguminosae
    Part used: dried ripe seeds
    Main constituents: physostigmine ,
    isophysostigmine, physovenine.
    Uses: These are the cholinesterase
    inhibitors and used as antidote for
    atropine poisoning.
    Also used to treat glaucoma.

    Vinca alkaloids
    B.S: Catharanthus roseus
    Common name: periwinkle
    Family: Apocynacea
    Part used: whole plant
    Constituents: Vincristine, Vinblastine
    Uses: these alkaloids have anticancer
    properties.

    Ergot alkaoids
    B.S: Claviceps purpurea
    Family: Hypocreales
    Part used: Dried sclerotium of the
    fungus
    Main constituents: Ergotamine,
    Ergometrine, Ergocristine
    Uses: Ergotamine is used to treat
    migraine and clustur headache.
    Ergometrine acts as oxytocic
    agent and also used in post-partal
    haemorrhage.
    Rauwolfia alkaloids
    B.S: Rauwolfia serpentina
    Common name: indian
    snakeroot
    Family: Apocyanacea
    Part used: leaves
    Constituents: serpentine,
    reserpine, ajmaline, ajmalacine,
    Uses: used as antihypertensive
    and antiarrhythmic agent.

    Biosynthesis of Vinca alkaloids

    Ergot alkaloids

    Quinoline alkaloids
    B.S: Cinchona Succirubra, C.
    calisaya, C. officinalis
    Common name; Quina
    Family: Rubiaceae
    Part used: Dried Bark
    Constituents: Quinine, quinidine,
    cinchonine, cinchonidine.
    Uses: Quinine is a classical
    antimalarial.
    Quinidine is used for cardiac
    arrythmias and atrial fabrillation.

    ALKALOIDS DERIVED FROM


    TYROSINE

    Isoquinoline alkaloids
    papaver alkaloids
    cephaelis alkaloids

    Papaver alkaloids Cephaelis alkaloids

    B.S: Papaver somniferum


    Family: papaveraceae
    Part used: dried milky latex of
    poppy capsule.
    constituents: Morphine,
    codiene, thebaine, Norcotine,
    Narciene, papaverine
    Uses: Morphine is used as
    analgesic.
    codiene is used in cough
    preparations.

    B.S: C.ipecacuanha
    Common name: Ipecac
    Part used: roots and rhizome
    Family: Rubiaceae
    Constituents: cephaline, psychotrine,
    Emetine,
    Uses: ipecacuanha is used as expectorant
    and emetic and in the treatment of
    Ameobic dysentry.

    Emetine

    BIOSYNTHESIS OF OPIUM
    ALKALOIDS:
    ------- L-Dopa ------ Dopamine

    +
    3,4 dipydroxyphenylpyruvic acid
    PAPAVERINE ----------------( ket intermediate)
    Reticuline
    Saluteridine

    Saluteredinol

    norlaudanosoline

    Alkaloids derived from


    phenylalanine
    EPHEDRINE,
    PSEUDOEPHEDRINE

    :-

    B.S It consists of dried young stem of


    Ephedra gerardiana and Ephedra
    nebrodensis.
    SynonymMa-huang).
    Family:- Ephedraceae
    C.C:-- It contains the amino alkaloids :
    Ephedrine, nor-ephedrine, n-methyl
    ephedrine, pseudo-ephedrine.
    Uses: it is used in Asthma, hay fever,
    flu, cold medications.

    Biosynthesis of Ephedrine

    END

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