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ALKALOIDS Means 'alkali like' hence resembles some characters like occurring complex amines i.e. containing one or more nitrogen atom. Method -1: Powdered drug Defatted, moistened & render alkaline with Na2Co3, NH3 (Alkaloids are freed as bases) Extract with org solvent eg. CHCl3, ether or methylene dichloride Total Extract Concentrate & shake well with succesive quantities of inorganic acid. Residual organic fraction (Like pigment, fats, very weak bases or CHCl3 soluble alkaloid Sulphates) Org solution of alkaloidal bases remove solvent (Crude alkaloid mixture) Purification by fractional crystallization Chromatographic seperation etc. Structure identification by modern analytical techniques like U.V., I.R, NMR, mass spectroscopy etc. Residual aquendes fraction aqueous acid solution (Alkaloidal salts) make alkaline & extract alkaloids with immiscible solvents
Method :-2 Plant material Ethanol Ethanol extract Treated with 2% HCL at room temp Aqueous fraction Diethylether Residue
Diethylether extract Flavonoids
Aqueous extract Basify with NH3 Extract with CHCl3 Alkaline soln Mayer's reagent (Mercuric chloride) + KI + H20) Alkaloid Treated with HCl Aqueous acidic soln
CHCl3 extract Alkaloid treated with Ba [OH]2 filter Sapoins & glycosides
Stass otto process (Mostly use & easier) Powdered crude drug moistened with H2O + treat with lime Alkaloidal freebases (From their acid salts) CH Cl3/ether
Organic solvent layer (Concentrated) Aqueous acid Alkaloid
aqueous layer (Alkaloidal salt) NH3 or aq KOH Liberate freebase Org. solvent Organic extract (Concentrated) Drying Total alkaloid
Method - 4 Manske's Process Powdered Crude drug Defatted with pet ether Residue CH3O H
Alcoholic extract Dissolve in Concentrated water & adjust PH2 Extract Steam distillation Dark sol or In Refrigerator Several days (to remove impurities) Filtrate ether/CHCl3 Remove non-alkaloidal Impurities Remove non alkaloidal impurities Basified Treat with CHCl3 or ether organic layer Evaporated Crude alkaloid heated with paraffin (to remove impurities)
Filtrate ether/CHCl3 To remove non alkaloidal impurities
Treat with CHCl3 or ether organic layer evaporated
GLYCOSIDES "Organic compound from plant or animal sources which on enzymatic or acid hydrolysis give one or more sugar moieties along with non-sugar moiety. The former called glycone & the later as aglycone or genin". Method - 1: Air dried plant material
Methanol (MeOH) Methanol extract into water
Soluble Extracted n- butanol n -butanol extract concetrated & ppt with acetone ppt contains mixture of Glycoside
Method - 2: Fresh plant material shake with n-butanol Shake with water and ethylacetate (1:1)
extract with evaporated ethylacetate invaccum Ethyl acetate Ethylacetate (insoluble) SiO2 column Glycoside
extract with n- butanol n-butanol extract SiO2 column Glycoside
Method - 3 :
Stass Otto method
Powdered drug For thermolabile Soxhlation with alcohol drugs below 450 C Extract For pptn lead acetate of tannins
lead actate sol For pptn of pass H2S Lead sulphide Extract filtered Crude Glycosides Purification Fractional solubility Fractional crystallization TLC & column chromatography
VOLATILE OILS i.e. TERPENES & TERPENOIDS: Also called as essential oil refers characteristic scent that develops the exalted feeling after in inhaling the fragrance. (A) Hydrodistillation - 4 methods of isolation are: Method - 1 :Water distillation Plant material at the bottom of container
Immersed in water closed boil vessel Extract (complete isolation not occur) Method -2 : Water & steam distillation Plant material lodged on perforated grid or screen Incontact with steam Decomposition of oil less yield of volatile oil more. Method ;- 3 : Steam distillation Plant material Peoforated supported on grid coils placed below grid Oils/Perfumes
* Condition 1. High pressure : Volatile oil likes to decompose (hydrolysis of ester) 2. Reduced presssure : Oils containing ester 3. Superheated steam distillation: Chemically stable compound.
Method - 4: Distillation per Se (terpentine) Plant material Org solvent/alcohol Resin remain is molten form and Support separation of less volatile fraction
Extraction of volatile oils is mainly done by means of "Clevenger apparatus.
DETERMINATION OF PERCENTAGE OF VOLATILE OIL IN DRUGS Setting of the apparatus: Apparatus for the determination of volatile oil in drugs consist of (i) A round- bottom 1 litre boiling flask (ii) A special still head. Still head contains: (i) Condenser (ii) receiver (iii) return tube. A side tube is also attached to introduce water in the graduated tube and return tube The official method for the estimation of volatile oil in a crude drug is hydrodistillation based on distilling the drug with water and distillate is collected in the graduated tube, from which the aqueous portion of the distillate automatically returns to distillation flask. Better results are obtained with some drugs by using 150 ml each of glycerine and water in place of pure after in the boiling flask. This modification should be used for dill, coriander, cloves, fennel and dried orange peel. When the oil is heavier than water (e.g. clove oil) a known volume of xylene is added to the graduated tube by a pipette which is passed through the side-tube of the still head. The increase in volume of xylene gives volume of oil distilled. Procedure: (i) Take 10 to 20g of powdered drug with 250 to 300 ml of water in distillation flask. Add a few pieces of porcelain to it (to avoid bumping during distillation) (ii) Set up the apparatus as represented in the figure. (iii) Fill the tubes (receiver and return tube) with water by introducing it at side tube by means of a pipette. Close the side tube. (iv) For heating the flask - Bunsen burner and asbestos filled wire gauge or heating mantle can be used. (v) Lift the flask at intervals and shake the contents, until the liquid is boiling steadily. Finally, adjust the flame so that the distillate in the graduated tube remains cold. Continue heating till no more oil collects . (This requires two hours or more). (vi) Turn out the gas and allow the liquid in the condenser to drain for five or ten minutes then read the volume of oil. Express the result as a volume in weight percentage. Diagram
Extraction with non-volatile solvents i.e. fat With out of heat (Enfluerage or absorption) used for extraction of delicate perfumes In wooden frame (chassis) supported with glass plate in the middle Spread fat layer of 3mm thickness (on either side of glass)
Spread layer of flower (petals) over fat layer Spread a fat layer over flower petals such 35-50 chassis filed over one another Flowers enclosed bet two layers of fats, release their aromatic components to fats. Length of exposure depends on flowers (Jasmine - 24 hours, Jonquil - 48 hours & Tuberose - 72 hours) After requiste time flowers are removed (fingers) or spatula Process repeated until suff. oil absorbed over fat Pomade (Product) with strong alcohol Oils & least traces of fats by freezing * Commonly used fat contains 40 parts of beef fat & 60 parts of lard.
Least traces of fats by freezing Residence (product) kept in freezer (to form ice) & immediately comes back it into room temp, so that water content or solvent may melt away. This process in continue until we get crude from of fat left behind. 2) With aid of heat (Maceration) Fats used like (beef fat, lard, olive oil or paraffin oil)
Flowers (Petals) immersed in fats (depend upto plant material) for 24-48 hours 50 - 700 C used hydraulic presses or centrifuges
Express fat Partly aromatised fat treated with fresh batches 10-15 times (until desired strength as to odour) Pomade (Product) Steam distillat (similar of vol oils) Oils * Used for reparation of oil from Roses Oranges blossoms, Lilies of the valley & violets. (C) Eculle Used for extract of citrus oils Oil Cells or seeds in rind Ruptured mechanically using pointed projections twisting raw material over them clockwise direction Product i.e. oil
TANNINS: Organic, non-nitrogenous plant product have astringent properties. Plant material For tannic acid H2O/alcohol alcoholic extract ether Etheral layer aqueous layer
(Gallic acid & ellagic acid) Concentrated
(True tannins) Concentrated
Subjected to isolation & purification by chromatography
RESINS Complex amorphous product which on heating first gets softened & then melts. Insoluble in most polar & non polar solvent, but dissolves in alcholed, rolvent ether, benzene & CHCl3 Crude drug alcohol alcoholic extract Add large Proportion concentrated H2O ppt of Resin Purification Resins
Definition: the term “alkaloid” (alkali-like) is commonly used to
designate basic heterocyclic nitrogenous compounds of plant origin that are physiologically active. 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, and Mescaline. Plant Origine: Some alkaloids are derived from Bacteria, Fungi, Insects, Frogs, and Animals. Or,
According to Landenberg "Alkaloids are defined as natural plant compounds that have a basic character and contain at least one nitrogen atom in a heterocyclic ring and having biological activities." Or, According to characteristic features “Alkaloids are basic nitrogenous plant origin, mostly optically active & possessing nitrogen hetero cycles as there structural units with physiological action.” Distribution and occurrence: Rare in lower plants. Dicots are richer in alkaloids than Monocots. Families rich in Alkaloids: Apocynaceae, Rubiaceae, Solanaceae and Papaveracea. Families free from Alkaloids: Rosaceae, Labiatae Distribution in Plant: • • • • • • • All Parts e.g. Datura. Barks e.g. Cinchona Seeds e.g. Nux vomica Roots e.g. Aconite Fruits e.g. Black pepper Leaves e.g. Tobacco Latex e.g. Opium
Forms of Alkaloids:
Free bases Salts with Organic acids e.g. Oxalic, acetic acids Salts with inorganic acids e.g. HCl, H2SO4. Salts with special acids: e.g. Meconic acid Quinic acid in Cinchona. Glycosidal form e.g. Solanine in Solanum. Function in Plants:
They may act as protective against insects and herbivores due to their
bitterness and toxicity. They are, in certain cases, the final products of detoxification (waste products). Source of nitrogen in case of nitrogen deficiency. They, sometimes, act as growth regulators in certain metabolic systems. They may be utilized as a source of energy in case of deficiency in carbon dioxide assimilation. Properties of Alkaloids
Physical Properties: Physical form or Nature: • 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. Color: • The majority of alkaloids are colorless but some are colored e.g.:Colchicine and berberine are yellow. • Canadine is orange. • The salts of sanguinarine are copper-red. 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, colchicines, pilocarpine and quaternary ammonium bases. • Bases insoluble or sparingly soluble in certain organic solvents: morphine in ether, theobromine and theophylline in benzene.
Isomerization: • Optically active isomers may show different physiological activities. L-ephedrine is 3.5 times more active than d-ephedrine. L-ergotamine is 3-4 times more active than d-ergotamine. D- Tubocurarine is more active than the corresponding L- form. Quinine (l-form) is antimalarial and its d- isomer quinidine is antiarrythmic. The racemic (optically inactive) dl-atropine is physiologically active. Chemical Properties: Alkaloid is basic in nature because of lone pair of electron on nitrogen atom. Nitrogen: • Primary amines R-NH2 e.g. Nor ephedrine • Secondary amines R2-NH e.g. Ephedrine • Tertiary amines R3-N e.g. Atropine • Quaternary ammonium salts R4-N e.g. d-Tubocurarine
Basicity: • R2-NH > R-NH2 > R3-N
• Saturated hexacyclic amines are more basic than aromatic amines. According to Basicity Alkaloids are classified into: • Weak bases e.g. Caffeine • Strong bases e.g. Atropine • Amphoteric e.g. Morphine • Neutral alkaloids e.g. Colchicines Oxygen: • Most alkaloids contain Oxygen and are solid in nature e.g. Atropine.
• Some alkaloids are free from Oxygen and are mostly liquids e.g. Nicotine, Coniine. Stability: • Effect of heat: Alkaloids are decomposed by heat, except Strychnine and caffeine (sublimable). • Reaction with acids: Salt formation. 2- Dilute acids hydrolyze Ester Alkaloids e.g. Atropine • Conc. acids may cause: Dehydration: Atropine → Apoatropine Morphine → Apomorphine • Effect of Alkalies: Dilute alkalis liberate most alkaloids from their salts e.g. NH3. They may cause Isomerization (racemization) of alkaloid as the conversion of Hyoscyamine to atropine. Strong alkalis: such as aqueous NaOH and KOH form salts with phenolic alkaloids. Strong alkalis cause hydrolysis of Ester alkaloids (e.g. atropine, cocaine and physostigmine) and Amide alkaloids (colchicines). Strong alkalis cause opening of lactones ring.
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