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PHYTOCHEMISTRY SECTIONS THIRD YEAR COURSE ALKALOIDS Introduction DEFINITION:    Alkaloids (mean alkali-like substances), Basic nitrogenous

compounds, Nitrogen in a heterocyclic ring system and a few do

not contain nitrogen in a ring system,   Of plant or animal origin Possessing a marked physiological action

Sources of alkaloids: a) Plant sources: The important alkaloid-bearing families are: Liliaceae,Amarylidaceae,Asteraceae,Ranunculaceae, Papaveraceae, Leguminosae, Rutaceae, Loganiaceae, Apocyanaceae, Solanaceae and Rubiaceae. • 

alkaloids occur in a salt form with organic or inorganic acids.g. Muscopyridine Musk deer. c) Marine sources Distribution of alkaloids: In general. Opium alkaloids occur with meconic acid Cinchona alkaloids with cinchotannic acid.g.g. Atropine from Atropa Species name: e. Some occur in combination with sugars as glycosides e.g. or in combination with specific acids e. 3) As waste products. solanine Function of alkaloids in plants: 1) Protective for the plant against insects 2) As end products of metabolism. their names may be derived from the: Genus name: e.g.b) Animal sources: Recently alkaloids were found in animals and insects e. Ergotamine from ergot Physiological activity: e.g. Cocaine from coca Common name: e. 4) Source for energy and reserve of nitrogen.g. Ergotamine and Ergometrine Ergot fungus. Emetine (emetic) . Lycopodine Lycopodium spores. Nomenclature: Alkaloids terminate with the suffix-ine. Pyocyanine Pseudomonas aeruginosa.

g. B) SUFFIXES: dine: Refer to isomerism as in the case of the Cinchona alkaloids.: Designates N-demethylation e.: Designates dehydration e.. epi . Seco . . Pelletierine from pelletier Sometimes prefixes and suffixes are usually added to describe related alkaloids: A) PREFIXES: Nor ..: means Ring opening.: Indicates different types of isomers. respectively.  Alkaloids are converted to their salts by aqueous mineral acids. pseudo . c) Free bases are soluble in organic solvents and insoluble in water. iso . apomorphine Neo . Classification of Alkaloids: Physicochemical Properties:  Physical characters: a) Alkaloids are crystalline solids.  Chemical characters: a) Basicity:  The basicity of alkaloids is due to the presence of a lone pair of electrons on the nitrogen atom. norpseudoephedrine and nornicotine Apo .. quinidine and cinchonidine are the optical isomers of quinine and cinchonine.g.g.Discoverer e. b) Colorless.

salts or N-oxides (NO). Primary amines: Norpseudoephedrine b. Tertiary amines: Atropine d. Bi. Mayer’s Reagent 2.H2SO4 and C. E. Phosphomolybdic acid 5.d add the colouring reagent. When the salt of an alkaloid is treated with hydroxyl ion. Dargendorff (Kraut’s) 4. Precipitating agents:  Alkaloids are ppted from their neutral or acidic solution by reagents contain heavy metals as Hg. 1. Erdmann’s reagent: Conc.HNO3  in a porcelin 1ml alkaloidal sol. Froehd’s reagent: Ammonium molybdate / conc. Tannic acid White ppt PPT. Wagner’s Reagent 3. Coloring agents:  Give characteristic colour with alkaloids and most contain C. in a test tube + 1ml dil HCl REAGENT 1. nitrogen gives up a hydrogen ion and the free amine is liberated. Alkaloids contain N atom either in a heterocyclic ring or in the side chain. H2SO4 2. Quaternary amines: Tubocurarine Detection of alkaloids: A. Secondary amines: Ephedrine c. Alkaloids occur as free bases. nitric acid / conc.t. a.  1ml alkaloidal sol. Creamy white ppt Brown ppt Orange to reddish White ppt brown ppt B. H2SO4 .

H2SO4 4. Marqui’s reagent : 4. Froehd’s reagent : 3. Erdmann’s reagent: -ve -ve -ve -ve 5. C. Phosphomolybidic acid: white ppt GENERAL COLOURING AGENTS : 1. PHARMACOLOGICAL ACTIONS : Anti-malarial. Mandalin’s reagent: Ammonium vanadate / conc. HNO3 reagent : yellow colour . QUININE NATURE : Dry Cinchona Bark. Mandalin’s reagent : 2. C. H2SO4  The colors formed are characteristic. The tests are sensitive to micro amounts and can be used for colorimetric assay.Ledgeriana Family : Rubiaceae. 1. STRUCTURE : GENERAL PPTING AGENTS : 1.3. Hgcl2 reagent : yellowish white ppt white ppt 5. Conc. Marquis‘ reagent: Formaldehyde / conc. Wagner’s reagent : reddish brown ppt 3. Tannic acid : 4. Mayer’s reagent : creamy white ppt 2. succirubra.