Alkaloids

•A precise definition of alkaloid is not available.

The term “alkaloid” (alkali-like) is commonly used
to designate basic heterocyclic nitrogenous
compounds of plant origin that are physiologically
active.
•Name of alkaloid ends in ‘ine’.
•Usually have bitter taste .
 Distribution and occurrence

• Rare in lower group of plants.

• Dicots are more rich in alkaloids than Monocots.
• Families rich in Alkaloids: Leguminosae,
Ranunculaceae, Apocynaceae, Rubiaceae,
Solanaceae, Berberidaceae and Papaveraceae.
• Families free from Alkaloids: Rosaceae, Labiatae
• Liliaceae,Amaryllidaceae among Monocot, Taxus
among Gymnosperm, also produce alkaloids.
 Classification
• Classified according to the nature of basic
chemical structures from which they derive.
• Two broad divisions :
• I. Non heterocyclic or atypical alkaloids,
sometimes called 'protalkaloids‘or biological
amines .
• II. Heterocyclic or typical alkaloids divided into
14 groups according to their ring structure.
 Physical Properties
• 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.
• 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 etc. Salts are usually
soluble in water and, insoluble or sparingly soluble in
organic solvents.
 Chemical Properties

• According to basicity Alkaloids are classified into:

Weak bases e.g. Caffeine , Strong bases e.g.
Atropine , Neutral alkaloids e.g. Colchicine
• 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.
• Effect of heat: Alkaloids are decomposed by heat,
except Strychnine and caffeine.
• Reaction with acids: 1- Salt formation. 2- Dilute
acids hydrolyze Ester Alkaloids e.g. Atropine
 Common amino acid precursors

• Phenylalanine
• Tyrosine
• Tryptophan
• Histidine
• Anthranilic acid
• Lysine
• Ornithine
 Indole Alkaloides
• Rauwolfia : reserpine, rescinnamine,
deserpidine
• Catharanthus: vinblastine, vincristine
• Nux vomica: strychnine, brucine
• Physostigma : physostigmine
• Ergot : ergotamine, ergonovine
1. Rauwolfia serpentina ( Sarpagandha)
• Rauwolfia serpentina L. Benth. Ex Kurz. Family
Apocyanaceae is an evergreen, woody,
glabrous and perennial shrub with maximum
height upto 60 cm. The plant possess tuberous
root with pale brown cork and elliptic to
lanceolate or obovate leaves in whorls of
three.
 Chemical Constituents
• R. serpentina root is reported to contain 0.7 – 3.0 % of total
alkaloids and about 0.1% of the active principle reserpine
which is an indole alkaloid, present in the root. Hence, root
biomass production of this plant could be of economic
importance.
• Rauwolfia alkaloids are classified into:
1. Indole alkaloids , 2. Indoline alkaloids
3. Indolenine alkaloids , 4. Oxyindole alkaloids
5. Pseudo indoxyl alkaloids
 Chemical Constituents
• Major alkaloids are Reserpine and Rescinnamine
• Other alkaloids are Ajmaline, Ajmalicine,
Rauwolfinine, Reserpinine,
Yohimbine, Serpentine and
Serpentinine
• Also contains Oleo-resin, Phytosterol, Fatty
acids, alcohol and sugars
One of the main alkaloids, reserpine, is used to treat hypertension
and certain types of mental illness
 Uses
• The alkaloids obtained from the root extract acts
directly on central nervous system and thereby
reduces blood pressure as compared to other
blood-pressure lowering agents.

• it is also used as a sedative in the treatment of

insomnia, anxiety, insanity and certain other
neuropsychiatric disorders.

• Used in the treatment of Circulatory disease like

obstruction of cerebral blood flow
2. Catharanthus roseus (L.) G. Don
• Catharanthus roseus is an evergreen
herbaceous plant .
• The leaves are oval to oblong, glossy green
hairless with a pale midrib and a short petiole
and they are arranged in the opposite pairs.
• The flowers are white to dark pink with a dark
red centre, with a basal tube and a corolla
with five petal like lobes.
• The fruit is a pair of follicles.
 Geographical Source

• Indigenous to Madagaskar, grows in India,

Africa, East Europe, Australia and India
• It is now common in many tropical and
subtropical regions worldwide, including the
Southern United states.
 Potentially Active Chemical
Constituents
• Alkaloids are the most potentially active
chemical constituents of Catharanthus roseus.
• More than 150 alkaloids are present in the
plant, which are used as pharmaceuticals,
agrochemicals, flavor and fragrance,
ingredients, food additives and pesticides.
• The alkaloids like Vinblastin, Vincrestine,
Vindesine, Vindeline Tabersonine etc. are
mainly present in aerial parts
• Vincristine and vinblastine have anti
neoplastic activity.
• Structure of Vinblastine and Vincristine are
quite similar ,differ only in N- formyl group
for N- methyl of Vinblastine. Vinblastine is
produced by coupling of the indole alkaloids
catharanthine and vindoline, both of which
occur free in the plant.
 Therapeutic Properties/ Uses
• Anti cancer property- The anticancer alkaloids Vinblastine
and Vincristine are derived from stem and leaf of
Catharanthus roseus.
• These alkaloids have growth inhibition effect to some
human tumors. They are responsible for arresting cell
division at metaphase stage. Both the alkaloids bind tightly
to tubulin and inhibit polymerization.
• Vinblastine is used experimentally for treatment of
neoplasmas and is recommended for Hodgkins disease,
chorio carcinoma.
• Vincristine another alkaloids is used for leukemia in
children.
• Vinblastine is sold as Velban or Vincristine as oncovin.
• Anti diabetic property- The ethanolic extracts of
the leaves and flower of C. roseus showed a
dose dependent lowering of blood sugar in
comparable to the standard drug.
• The Hypo glycemic effect has appeared due to
the result of the increase glucose utilization in
the liver.
• Anti oxidant property- Catharanthus roseus
contains significant amounts of volatile and
phenolic compounds including caffeoylquinic
acids and flavonol glycosides which are known
to possess antioxidant activity