GLYCOSIDES

A substance which on hydrolysis

 yields a reducing sugar (glycone)

- Glucose

- Rhamnose

- Digitoxose

- Fructose

 Deoxysugar

- Cymarose
  + one or more non-sugar substances
(genin/aglycone)
• Known as the aromatic aglycone or
genin portion
 found to exert a wide spectrum of
therapeutic actions, both in modern
medicines and in traditional medicaments,
ranging from cardiotonic, analgesic,
purgative, and anti-rheumatic, demulcent
and host of other useful actions.
 hydrolysis occurred in various ways:
 boiling with mineral acid
 by an enzyme
a. Emulsin - Bitter almond seeds.
b- Myrosin or Myrosinase - black
mustard seeds.
c- Rhamnase - glycosides containing
rhamnose as sugar part.
 other physiologic activities of the cells
that bring the enzyme in contact with
glycoside
o injury to the tissue
o germination process
 Solubility:
glycosides are water soluble compounds
and insoluble in the organic solvents.
Glycone part: water soluble, insoluble in
the organic solvents.
Aglycone part: water insoluble, soluble in
the organic solvents.
- ethyl acetate (best solvent for extraction)
 physico-chemical properties of
glycosides (general)
 Colorless, solid, amorphous, nonvolatile
(flavonoid- yellow, anthraquinone-red or
orange).
 Give positive reaction with Molisch's and
Fehling's solution test (after hydrolysis) –
brick-red precipitates (sugar component).
 Most of them have bitter taste
(except: populin, glycyrrhizin, stevioside).
 Odorless except saponin (glycyrrhizin).
 when a glycosides has a lot of sugars its
solubility in water decrease.
 The function or the role of
glycosides in the plant organism
 Converting toxic materials to non or less toxic.
 Source of energy (sugar reservoir).
 Storing harmful products such as phenol.
 Regulation for certain functions(growth).
 Some have beautiful colors (pollenation
process).
 Some glycosides have antibacterial activity, so
they protect the plants from bacteria and
diseases.
CLASSIFICATIONS
 (i) Anthracene glycosides
 (ii) Phenol glycosides
 (iii) Steroid glycosides
 (iv) Flavonoid glycosides
 (v) Coumarin and Furanocoumarin glycosides
 (vi) Cyanogenetic glycosides
 (vii) Thioglycosides
 (viii) Saponin glycosides
 (ix) Aldehyde glycosides
 (x) Alcohol glycosides
 (xi) Bitter glycosides
 (xii) Miscellaneous glycosides
TEST FOR GLYCOSIDES
 Cardio-Active Glycosides
 A small group of plant
glycosides act directly
on the heart muscle.
 These include (but are
not limited to cardiac
glycosides or
cardenolides)
 Cardenolides are
steroidal glycosides 
exert a slowing and
strengthening effect on
the failing cardiac
muscle.
 TYPES OF AGLYCONE
5-MEMBERED 6-MEMBERED
LACTONE RING LACTONE RING
 Cardenolides  Bufadienolides
 most prevalent in  also known as
nature “cardiac glycosides:
since it affect the
muscle of the heart
 Bufalin (isolated from
the skin of toads, Bufo
STRUCTURE OF CARDIAC
GLYCOSIDES
R – group defines the class of
Cardiac Glycosides
Pharmacological Action of Cardiac
Glycosides
 Effectiveness depends on both the
aglycones and the sugar attachments.
 Medicinal action depends on the aglycone
 But the sugars make the compound more
soluble and increases the fixation of the
glycoside to the heart muscle
Pharmacological Action of Cardiac
Glycosides
 It is thought to act in competition with K ions for specific
receptor enzymes (ATPase) sites in the cell membranes
of the heart muscle when there is an influx of Na ions.

 Effect is to increase the force of heart contraction

 Diuretic action relates to the improved circulatory effects.

A. DIGITALIS
 CARDIAC GLYCOSIDES
 Digitalis purpurea
(Digitalis, Purple
Foxglove, Fairy gloves,
Digifortis, Digitora, Pil-
Digis, Neodigitals) -
Scrophulariaceae
 Other uses of the plant
(and glycoside) include
being used as arrow
poisonings.
 Digitalis purpurea – Purple
Foxglove
 Definition:
 Digitalis consists of
the dried leaves of
Digitalis purpurea.
 It is required to
contain at least 0.3%
of total cardenolides
calculated as
digitoxin.
 Digitalis purpurea - Collection
 There is a general belief that the
pharmacological activity of the leaves increase
during the course of the day to reach a
maximum in the early afternoon (when they
should be harvested).

 This was supported by assays done in 1956

which showed a greater activity of the leaves at
noon than 8am, irrespective of if the leaves
where in the sun or shade.
 Active Constituents
 Primary glycosides
 purpurea glycoside A
 digitoxin
 purpurea glycoside B
 gitoxin
o Purpurea glycoside C
• Gitalin

• FURTHER HYDROLYSIS --------yield the

Secondary glycosides
 Secondary glycosides
 digitoxigenin,
 gitoxigenin
 gitaligenin or gitaloxigenin
 crude drug also contains a good number
of other glycosides (e.g.; digitalin, diginin);
saponins (e.g.; digitonin, gitin and
digitosaponin); flavonoids, tannins, gallic,
formic, acetic, succinic and benzoic acids;
fatty acids and enzyme digipuridase solely
responsible for hydrolysis of purpurea
glycosides
 Active Constituents
 other glycosides (present in smaller
quantities) include

 Digitalose
 Glucose
 Verdoxin (x3 more toxic than gitaloxigenin)
 Digitalis – Medicinal Actions
 tonic effect on the diseased heart

 glycosides enable the heart to beat more

strongly, slowly and regularly, without
using or needing more O2.

 Stimulates urine production  lessening

the load on the heart.
 Digitalis purpurea
 Cautions

 Potential for overdose

 Only under professional supervision

 Plant is subject to legal restrictions.

ADULTERANTS
1.Great mullein leaves: The leaves of Verbascum
thapsus belonging to the family Scrophularineae
2.Primose leaves: The leaves of Primula vulgaris
belonging to the family Primulaceae
3.Comfrey leaves: The leaves of Symphytum
officinale belonging to the family Boraginaceae
 are invariably mixed to digitalis
ALLIED DRUGS OF DIGITALIS
 Digitalis Lanata– Woolly Foxglove Leaf ,
Austrial Digitalis or Grecian Foxglove

 today’s main source of cardiac

glycosides (digoxin)
 Digoxin – most widely
cardiotonic glycosides
and highly potent.
The drug is almost three times more potent
in comparison to Digitalis
 purpurea
Digitalis lanata
 Biological Source:
 The dried leaves of Digitalis lanata Ehrhart,
belonging to family Scrophularineae.
 Chemical Constituents:
 Chemically pure primary glycosides:
 Lanatoside A (Diginalis A)
 Lanatoside B (Diginalis B)
 Lanatoside C (Diginalis C)
 Digitalis lutea – Straw foxglove
 The dried leaves of Digitalis lutea Linn.
belonging to family Scrophulariacea
 Uses
 It is used as a common substitute for the
official drug.
 It is potent as Digitalis purpurea.
 It is mostly used for the same purpose as
that of Digitalis purpurea , but it is found to
exert much lesser irritation.
 Digitalis Thapsi – Spanish Foxglove,
Spanish digitalis
 The dried leaves of Digitalis thapsi Linn.
belonging to the family Scrophulariacea.
 Uses:
 Its therapeutic efficacy is almost 1.25 to 3
times more potent than Digitalis purpurea
and its actions are similar
B. SQUILL
 EUROPEAN SQUILL - Sea, onion, Bulbus
Scillae; Meerzweibel, White Squill, Squil
bulb; Scila
 fleshy inner bulb scales of the white
variety of Urginea maritima (L.) Baker
(Scilla maritima L.) belonging to family
Liliaceae
 Chemical Constituents:
 Squill has the following glycosides,namely:
 Glucoscillaren A = Scillarenin + Rhamnose
+ Glucose + Glucose;
 Scillaren A = Scillarenin + Rhamnose +
Glucose;
 Proscillaridin A = Scillarenin + Rhamnose.
 the drug also comprises of flavonoids,
calcium oxalate, xanthoscillide, sinistrin
(an inulin like carbohydrate) and an
irritation causing volatile component.
 Steps Involved in the Acidic and
Enzymatic Hydrolysis of Scillaren A
 Stoll in 1933 was first able to separate and
isolate two glycosides in their purest
form, namely: Scillaren A and Scillaren
B. These two naturally occurring glyosides
are usually present in the crude drug in the
ratio 2:1 (i.e., 2 parts of Scillaren A and 1
part of Scillaren B).
 Chemical Test:Scillaren A on interaction with
acetic anhydride and H2SO4, it gives rise to a
red color which changes gradually first to blue
and finally to bluish green color.
 Uses
 It is a potent cardiotonic without having any
cumulative effect (unlike Digitalis).
 It is mostly employed in small doses as an effective
expectorant specially in chronic bronchitis.
 It causes emesis in relatively higher doses.
 The squill glycosides usually produce copious
diuresis.
 By virtue of the fact that the squill glycosides
possess high therapeutic index and rapid
elimination
they invariably maintain compensation in such
patients where a prolonged treatment is required
 Indian Squill - Scilla; Sea onion; Jangli
Pyaj; Urginae
 the dried slices of the bulbs of Urginbea
indica Kunth; belonging to the family
Liliaceae.
 Chemical Constituents:
 essentially comprises of cardiac glycosides
(0.3%), alcohol soluble extractives (20-40%),
mucilages (40%) and calcium oxalate.
 The two major cardiac glycosides present in the
drug are Scillaren A and Scillaren B
 Red Squill
 red variety of European squill Urginea
maritima (L.) Baker belonging to family
Liliaceae.
 the red color is attributed due to the
presence of anthocyanin pigments present
in the mesophyll cells of scales
 glycoside present in the red squill is known
as scilliroside
 poisonous
 It is slightly soluble in water, but is soluble
freely in lower alcohol, ethylene glycol,
dioxane and glacial acetic acid.
 It is mostly used as a rat poison.
 C. STROPHANTUS
 Synonym: Semino stropanthi
 dried and ripe seeds of Strophanthus
hispidus De Candolle or Strophanthus
kombe Oliver, belonging to the family
Apocynaceae
 Chemical Constituents The seeds of
strophanthus usually contain three vital
glycosides, namely: K-strophanthoside, K-
strophanthride b and cymarin. Interestingly, all
these glycosides undergo hydrolysis to yield
strophanthidin (aglycone).
 K-Strophanthoside is the main constituent
of Strophantus.kombe
 Acidic hydrolysis of K-strophanthoside gives rise to the
aglycone strophanthidin along with a triose sugar known
as strophanthotriose that comprise of one mole of
cymarose and two moles of glucose.
 Enzymatic hydrolysis of K-strophanthoside using the
enzymes-glucosidase, usually present in yeast, helps in
cleaving off the terminal a-D glucose thereby yielding the
secondary glycoside known as K-strophanthidin b.
Further hydrolysis of the resulting product with
strophanthobiase, the former yields the glycosides
cymarin which comprises of the aglycone strophanthidin
along with one mole each of cymarin and b-D-glucose.
 Chemical Tests
 Generally, the strophanthus glycosides exhibit an
emerald green coloration on the addition of sulphuric
acid.
 Dissolve about 0.1g of strophanthidin in 5 ml of water
and add to it a few drops of ferric chloride solution
followed by a 1-2 ml of concentrated sulphuric acid; the
appearance of an initial red precipitate that finally turns
green within a period of 1-2 hours.
 To 50 mg of strophanthidin add 5 ml of water, shake and
add 2 ml of 2% tannic acid solution, the appearance of a
distinct precipitate affirms its presence.
 It shows positive Baljet Test, Legal Test and Keller
Killiani Test
 Uses
 It is used intravenously for treating
emergency cardiac conditions. However,
orally strophanthidin is not so active.
 These glycosides have been found to
exert less cumulative effect unlike the
digitalis glycosides.
 Overall their therapeutic actions are very
much similar to those of Digitalis.
 Allied Drugs
 G-Strophanthin - Ouabain; Gratus
strophanthin; Acocantherin; Gratibain;
Astrobain; Purostrophan; Strophoperim;
Strodiral
 obtained from the seeds of Strophanthus
gratus (Wall & Hock) Baill. It also occurs in
the wood of Acokanthera ouabio Cathel
and A. schumperi belonging to the family
Apocynaceae.
 seeds contain the glycoside G-
strophanthin (or Ouabain)
 seeds contain the glycoside G-
strophanthin (or Ouabain)
 Ouabain on hydrolysis gives rise to an
aglycone termed as G-strophanthidin (or
Ouabagenin) and L-rhamnose as the
residual sugar moiety.
 Chemical Tests
 Mix a few crystals of quabain with a mixture of
conc. H2SO4 and water (4:1), the appearance of
a brownish red color, which deepens slowly and
ultimately shows a green fluorescence.
 Froehde’s Test: Mix a few crystals with a drop of
Froehde’s reagent, evaporate to dryness, cool
and add a drop of H2SO4—the development of
a blue color takes place.
 Mandalin’s Test: Moisten a few crystals with
Mandalin’s reagent, evaporate to dryness, cool
and then add one drop of conc. H2SO4—the
appearance of a green color occurs.
 Uses
 It is an important cardiotonic, which is usually
administered intravenously in acute cardiac
failure, due to its inherent rapid onset of action.
 It is invariably employed as a ‘reference
standard’ for comparison of cardiac glycosides.
 It also exerts diuretic action.
 OTHER PLANT SOURCE
 Convallaria majalis – (Liliaceae)
 also known as lily of the
valley root
 cardioactive properties
similar to Digitalis, but
less cumulative
 Convallaria majalis – lily of the
valley
 Parts used:

 Collected parts
include
 aerial parts (when
flowers begin to open)
 rhizomes & roots
 Convallaria majalis – Constituents
 Glycosides (highest in
flowering period)
 Convallatoxin  Convallatoxin
 On hydrolysis give
• Strophanthidin
• & (-) – rhamnose

 minor cardenolides (±40

glycosides)
 Convalloside (seed)
 Convallatoxol

 Saponins –
convallamaroside
 Flavonoids
 Convallaria – Pharmacological
Effects
strengthens contraction
of heart muscle

 lowers internal heart

pressure

 increases cardiac
efficiency

 venotonic
 Convallaria - Cautions
 very toxic
 only administered by
professionals.

 may cause nausea,

vomiting & GIT symptoms
if taken in large amounts

 Because Convallaria
cardenolides are poorly
absorbed in the stomach
and intestines they are
rarely deadly.
 Apocynum, black
indian hemp, dog
bane, or canadian
hemp
 dried rhizome of and
roots of Apocynum
cannabinum or
Apocynum
androsaemifolium
(Apocynaceae)
 Cymarin (active)
 Apocannaoside and
Cyanocannoside
(minor)
 Adonis or pheasant’s
eye
 dried overground
portion or Adonis
vernalis
(Ranunculaceae)
 Adonitoxin, cymarin
and K-strophanthin
 Cactus grandiflorus or
night blooming cereus
 fresh, succulent stem
of wild-growing
Selenicereus
grandiflorus
(Cactaceae)
 Black hellebore or
Christmas rose
 dried rhizome and
roots of Helleborus
niger
(Ranunculaceae)
 Hellebrin ( chief)
 cardiac stimulant
 Nerium oleander
(Apocynaceae)
 Oleandrin (derivative
of gitoxigenin)