SECONDARY

METABOLITES
B.Pharm Semester 3
Pharmacognosy & Phytochemistry I
BP305TP

1 Prepared By:
Ms. Priya Shah
Assistant Professor
L. J. Institute of Pharmacy
 ALKALOIDS

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 DEFINATION
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Alkaloid is defined as organic products of natural or

synthetic origin which are basic in nature (alkali-like) , and
contain one or more nitrogen atoms in heterocyclic ring,
and possess specific physiological actions on human or
animal body, when used in small quantities.
 DISTRIBUTION AND OCCURRENCE
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Rare in lower plants.

Dicots are more rich in alkaloids than Monocots.

Families rich in Alkaloids:

Alkaloids Apocynaceae, Rubiaceae,
Solanaceae and Papaveracea.
Papaveracea

Families free from Alkaloids:

Alkaloids Rosaceae, Labiatae
 DISTRIBUTION IN PLANTS
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PLANT PART EXAMPLE

All Parts Datura
Barks Cinchona
Seeds Nux Vomica
Roots Aconite
Fruits Black peppe
Leaves Tobacco
Latex Opium
 PHYSICAL PROPERTIES
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Colorless, crystalline solid with sharp melting point.

Some alkaloids are amorphous solids while other like

coniine, nicotine are liquid in nature.

Some alkaloid are color in nature, eg. Betanidine shows

red color, Berberine shows yellow color.

Salt of most alkaloid are soluble in water.

Free bases are insoluble in water and their salts are very
sparingly soluble in organic solvent.
 CONTD…
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Quaternary bases are only water soluble

Pseudo and proto alkaloid give higher solubility in water

Solubility and salts of alkaloid is useful in pharmaceutical

industry for extraction

They give color precipitate with halogenated compound

 CONTD…
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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.

Quinine (l-form) is antimalarial and its d- isomer quinidine

is antiarrhythmic. The racemic (optically inactive) dl-
atropine is physiologically active.
 CHEMICAL PROPERTIES
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Basic in reaction

Turns to be neutral or acidic when adjacent functional

groups are electron withdrawing like amide group.

Salt formation with inorganic Acid – their decomposition

during their storage

Contain 1 or more N

In natural form – exist either in free state as amine or as

salt with acid or alkaloidal N-oxide
 CHEMICAL TESTS
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1) DRAGENDORFF’S REAGENTS:
REAGENTS (Potassium bismuth iodide
solution) giving reddish brown precipitate.

2) MAYER REAGENT: (Potassium mercuric iodine solution)

giving cream colored precipitate.
precipitate

3) WAGNER REAGENT:
REAGENT (Iodine and potassium iodide
solution) yielding reddish brown precipitate.

4) HAGER REAGENT: give yellow precipitate with picric acid.

 CHEMICAL TESTS
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5) MUREXIDE TEST: Purine Alkaloids

6) VAN URK’S TEST: Ergot alkaloids

7) VITALI MORIN TEST: Tropane alkaloids

8) THELLOQUINE TEST: Quinine

 TYPES OF ALKALOID
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A) Biosynthetic classification

B) Chemical classification

a) True alkaloid

b) Proto alkaloid

c) Pseudo alkaloid

C) Taxonomical classification

D) Pharmacological classification
 A) BIOSYNTHETIC CLASSIFICATION
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Examples:

1) Indole alkaloids - Tryptophan

2) Piperidine alkaloids - Lysine

3) Imidazole alkaloid - Histidine

4) Phenylethyl amine alkaloids - Tyrosine

 CLASSIFICATION
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 CHEMICAL CLASSIFICATION
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 CONTD…
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 CONTD…
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 CONTD…
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 ALKALOIDS OF IMPORTANT DRUGS
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Drug Source Active constituents Uses

A fungal sclerotium Ergotamine,

Ergot Oxytocic
of Clavicep purpurea Ergometrine

Strychnous nux Bitter, Tonic,

Nux vomica seeds Strychnine
vomica Stimulant
Vincristrine, Anticancer,
Vinca Catharanthus roseus
Vinblastine Leukemia
Vasicine, Antitussive,
Vasaka Leaves Adhatoda vasaka
Vasicinone Expectorant
Cinchona calisaya,
Quinine, Quinidine,
C. officinalis,
officinalis Antimalarial, Bitter,
Cinchona Cinchonine,
C. ledgeriana Tonic
Cinchonidine
C. succirubra
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VOLATILE OIL
 DEFINITION
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“The Volatile oils ” are those oils which are diffusing readily
into the air where oil may be detected by their smell.
Chemistry of volatile oils;;
They evaporated when exposed to air at temperature of
15.5 to 16.50◦c, so they are called as “Ethereal oils.”
They represent essence Or Active constituents of plant,
Hence they are also known as “Essential oils.”
Chemically, they are derived from terpenes and their
Oxygenated compounds..
 PROPERTIES
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Diffusing readily into air at room temperature.

Soluble in alcohol, ether, other organic solvents.

Slightly miscible with water and usually lighter than water.

Most of them are optically active.

Detected by smell receptors.

receptors
 CONTD…
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Liable to deterioration especially resinification & peroxide
formation

Solid essential oil – Stearoptene e.g. Thymol,Camphor

Liquid essential oil – Eleoptene

Volatile oils are obtained by distillation method with

Clavenger’s apparatus
 IDENTIFICATION TESTS
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1. Thin section + alcoholic sol. of sudanIII – red colour

2. Thin section + drop of tincture alkane – red colour

Separate volatile oil from distillate and perform following

tests.

a) Filter paper is not permanently stained with volatile oil.

 CONTD…
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b) Solubility test :

Volatile oil are soluble in alcohol, ether and other organic

solvent and insoluble in water.
water

It is also two type identify

1) PHYSICAL CHARACTERISTICS.

2) CHEMICAL CHARACTERISTICS.
CHARACTERISTICS
 PHYSICAL CHARACTERISTICS
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Following physical properties of the volatile oils are
generally important for the quality control.

Boiling point.

Refractive index.

Optical rotation.

Specific gravity.

Freezing point.

Solubility characteristics.
characteristics
 CHEMICAL CHARACTERISTICS
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UV-Visible spectroscopy,

IR-spectroscopy,

NMR-spectroscopy,

GC-spectroscopy,

HPLC-analysis,

MASS-spectroscopy,

HPTLC
 DIFFERENCE
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 CONTD…
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 CLASSIFICATION
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CLASS EXAMPLES
Hydrocarbon Turpentine oil
Alcohol volatile oil Sandal wood oil, Pepppermint oil, Coriander
Aldehyde volatile oil Lemon grass oil, lemon peel, orange peel
Ester volatile oil Gaultheria, lavender, mustard
Hydrocarbon volatile Turpentine, black papper
oil
Ketone volatile oil Caraway, spearmint, camphor
Oxide volatile oil Chenopodium - Anthelmintic
Eucalyptus - counter irritant
Phenolic ester volatile Fennel - stimulant, carminative
oil Nutmeg - stimulant, carminative
Phenol volatile oil Clove, thyme
 CHEMICAL TEST
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Thin section of drug on treatment with alcoholic solution of

Sudan III develops red colour in the presence of volatile

oils.
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