Glycosides

Dr Rokeya Sultana
Prof and HOD
Dept. of Pharmacgnosy

Yenepoya Pharmacy College & Research Centre

Yenepoya (Deemed to be University), Deralakatte, Mangaluru
 Table of Content
• General introduction of Glycosides

• Definition

• Chemical composition

• Chemistry & chemical classes of Glycosides

• Occurance and distribution

• Properties
YPCRC 2
 Specific Learning Objectives
• Learn general introduction and composition of
glycosides.

• Understand Definition and properties of glycosides.

•
• Remember Chemistry & chemical classes of
glycosides

• Understand different types of glycosides such as

Cardiac Glycosides, Steroids, Triterpenoids,
Naphthaquinones Phenyl Propanoids and Flavonoids.
YPCRC 3
 Definition
• Organic natural compounds present in a lot of
plants and some animals, these compounds
upon hydrolysis give one or more sugars
(glycone) β- form and non sugar (aglycone) or
called genin.

YPCRC 4
 Introduction

A glycoside is any molecule in which

a sugar group is bonded through its
anomeric carbon to another group via
glycosidic bond.

A glycosidic bond is a certain type of

chemical bond that joins a sugar
molecule to another molecule.

A substance containing a glycosidic

bond is a glycoside.

The sugar group -glycone and the

nonsugar group -aglycone or genin.

YPCRC 5
 Sugar part
The sugars found in glycosides may be glucose and
rhamnose (monosaccharides) more rarely, deoxysugars
such as the digitoxose or cymarose found in cardiac
glycosides.

By the nature of the sugar glycosides are divided into two

groups:

• Piranosides
• Furanosides.

There are also α-and β-glycosides depending on the

configuration of carbon connected
YPCRC
to the aglycone. 6
 Sugar part
• Sugar part of the molecules may contain one or
more interconnected sugars (monosaccharides,
disaccharides, etc.)

• Pentosides - pentose glycosides.

• Hexosides - hexose glycosides.

• Biosides - glycosides of disaccharides.

YPCRC 7
 Non sugar part
• Aglycone

• Medicinal property

YPCRC 8
 Classification
• On the basis of the linkage between glycone and
aglycone part

• Classification of glycosides based on glycone part

• Classification of glycosides based on chemical

nature of aglycon part

• Classifications of glycosides based on their

therapeutic effects

YPCRC 9
 Linkage between Glycone and Aglycone
part
• S-glycosides : In these glycosides the sugar
attached to a Sulfur atom of aglycone ,for example
sinigrin.

• N-glycosides : In these glycosides the sugar linked

with Nitrogen atom of (-NH2,-NH-)amino group of
aglycone ,for example nucleosides DNA,RNA.

YPCRC 10
Linkage between Glycone and Aglycone
part

• C-glycosides : In these glycosides the sugar

linked (condensed) directly to Carbon atom of
aglycone ,for example aloin.

• O-glycosides : In these glycosides the sugar part

is linked with a oxygen atom of aglycone .

YPCRC 11
 Classification of glycosides based on Glycone part

• Glucose - Sennoside.

• Rhamnose - frangullin.

• Digitoxose - digoxin.

• Glucose and Rhammnose Glucorhamnoside -

glucofrangulin.

• Rhamnose and glucose - Rhamnoglucoside -Rutin.

YPCRC 12
 Based on chemical group
• Anthraquinone group - Anthracene derivatives
(purgatives)---- Aloe, Senna, Cascara.

• Cardinolides & Bufadienolides (Lactone) - Cardiac

glycosides (poisons) from Digitalis, squill.

• Triterpenoid glycosides or saponin glycosides: A

triterpene molecule is condensed with a sugar
component. E. g. glycyrrhizin

YPCRC 13
 Based on chemical group
• Sterol or cardiac glycoside: - aglycon portion is steroid
molecule. Ex: digitalis.

• Saponins (soaps) aglycone = trans-linked steroid,

Ginsang Dioscorea .

• Coumarins cyclooxygenase inhibitors e.g..Ammi,

Visanga

YPCRC 14
 Based on chemical group

• Isothiocyanate glycosides: isothiocyanate glycosides

contain a part which is constituted with
allylisothiocyanate (-S=C=N-) like sinigrin or sinalbin

• Flavonoid glycosides: A flavone ,flavonol, flavanone

aglycone is present in these glycosides. E.g. Rutin,
Hesperidin.

• Phenolic analgesics – aspirin.

YPCRC 15
 Based on chemical group
• Alcohol glycosides: if aglycone part is alcohol -this
group called alcoholic group like Salicin, populin

• Cyanogenic compounds --- Bitter almond , Wild cherry

• Aldehyde glycoside. Ex: vanilla pods.

• Lactone glycoside. Ex: Cantharide.

YPCRC 16
 Based on their therapeutic effects

• CHF(Congestive Heart Failure)and cardiac muscles

stimulators
– Digitalis glycosides: digoxin, digitoxin, gitoxin (Fox
glove leaves).
– Ouabain: Strophanthus gratus seeds.
– c. K-strophanthin -Strophanthus kombe seeds.
– d. Scillaren A,B which isolated from red and white
Squill bulbs.

YPCRC 17
 Based on their therapeutic effects
• Laxative group of glycosides
– Sennoside A,B,C,D (Senna leaves and fruits).
– Cascaroside A,B (Cascara bark).
– Aloin and barbaloin (Aloe vera and Aloe
barbadensis juice)

• Local irritant group :Sinigrin (Black mustered

seeds-Brassica nigra)

YPCRC 18
 Based on their therapeutic effects

• Analgesics and antipyretics : Salicin Salisylic acid

- Willow or Salix bark.

• Anti-inflammatory group : Aloin for acne

Glycyrrhizin for peptic ulcer

YPCRC 19
 Occurance and distribution
 Leaf - Senna , Digitalis

 Stem – Chirata

 Bark – Cascara

 Wood - Quassia

 Flower – Saffron

YPCRC 20
 Occurrence and distribution
 Fruits – Ajwan

 Seed – Bitter almond

 Root - Liquorice, Rhubarb

 Tubers – Dioscorea

 Juice – Aloe vera

YPCRC 21
Leaf Senna (Anthraquinone glycoside)

https://en.wikipedia.org/wiki/Senna

YPCRC 22
Leaf Digitalis( cardiac glycosides)

https://en.wikipedia.org/wiki/Digitalis

YPCRC 23
Chirata stem(Secoiridoid glycoside)

Swertiamarin

https://en.wikipedia.org/wiki/chirata

YPCRC 24
Flower Saffron Terpene glycosides

https://en.wikipedia.org/wiki/Safron

YPCRC 25
 Fruit Ajwan Coumerin glycoside

Khellin

https://en.wikipedia.org/wiki/Ajwan

YPCRC 26
Bark Cascara (Anthraquinone glycosie)

Cascaroside A

https://en.wikipedia.org/wiki/cascera

YPCRC 27
Liquorice root (Saponin glycoside)

https://en.wikipedia.org/wiki/liquorice

YPCRC 28
 Diacoria Tuber

https://en.wikipedia.org/wiki/Diosgenin

YPCRC 29
 Properties
• Colorless, solid, amorphous, nonvolatile (flavonoid-
yellow, anthraquinone-red or orange)

• Most of them have bitter taste.(except: populin,

glycyrrhizin, stevioside).

• Odorless except saponin (glycyrrhizin).

• Glycosides are water soluble, insoluble in the organic

solvents
YPCRC 30
 Properties
• Glycone part: water soluble, insoluble in organic solvents

• Aglycone part: water insoluble, soluble in organic solvents.

• Give positive reaction with Molisch's and Fehling's solution

test (after hydrolysis).

• when a glycosides has a lot of sugars its solubility in water

decrease.

• Glycosides hydrolyzed by using mineral acids and

temperature or by using enzymes
YPCRC 31
 Identification by chemical test
• Cardiac
• Anthraquinone
• Flavonoid
• Saponin
• Steroid
• Cyanogenetic
• Titerpenoid glycosides
• Coumarin

YPCRC 32
 Test for Cardiac Glycosides
 Baljet’s test –Section of drug + sodium picrate solution  yellow
to orange color.

 Legal’s test –Aqueous or alcoholic extract+1ml pyridine +1 ml

sodium nitroprussidePink to red color.

 Keller – killiani test – to 2 ml extract+glacial acetic acid+one

drop of 5% Fecl3 & conc. H2sO4 Reddish brown color appears
at junction of two liquid.

 Kedde’s test - 1ml of test solution + 2ml reagent (3,5-dinitro

benzene carboxylic acid) - Bluish to purple color
 Test for Anthraquinone Glycosides
• Borntrager’s test - Drug+ H2SO4+ boil on water bath for 10
min +cool +3 ml of benzene + shake well+Keep aside for
some time+ Collect the organic layer from top +1 ml
ammonium hydroxide and shake  Cherry pink color
observed in lower ammonical layer .

• Modified Borntrager’s test - Drug + Fecl3 + HCl+boil on water

bath for 10 min +cool +3 ml of benzene + shake well. Keep a
side for sometime +Collect the organic layer from top +1 ml
ammonium hydroxide + shake Cherry pink color observed in
lower ammonical layer
 Test for Flavonoids
• Shinoda test – the dried extracts were dissolved in 95%
ethanol and few drops of concentrated hydrochloric acid were
added. Then the magnesium turnings were put into the
solution and observed for appearance of pink color

Test for Saponin Glycosides

• Foam test – shake the drug extract or dry powder vigorously
with water. Persistent stable foam is observed
• Hemolytic test - Add drug extract or dry powder to one drop
of blood placed on the glass slide. Hemolytic zone appears
 Test for Steroids glycosides
• Salkowski test – 5ml extract is mixed with 2 ml chloroform &
3 ml H2S04 was added to form a layer . The reddish brown
coloration of the interface was formed to show positive
results

• Liebarmann-Burchard reaction – Mix 2ml extract with

chloroform. Add 1-2 ml of acetic anhydride & 2 drops of
conc. H2SO4 from the side of the test tube. First red, then
blue and finally green colour appears
 Test for Cyanogenetic glycoside
• Sodium Picrate test : Small amount of drug sample →
humidification with water in a conical flask + few drops of
conc. H2SO4 → appearance of brick colour → presence
of cynophoric glycoside.

• Feeriferrocyanide test: 1 gm of drug sample + 5 ml of

alcoholic KOH → transfer it to aqueous solution of
FeSO4 and FeCl3 → keep it on room temperature for10
minutes. → transfer whole solution to 20 % HCl
→appearance of Prussian blue colour → the presence of
cynogenetic glycosides .
YPCRC 37
 Test for Triterpenoid glycoside
• Antimony trichloride test: An alcoholic extract of drug
→evaporate → dry → make extract with chloroform +
saturated solution of antimony trichloride in
chloroform containing 20% acetic anhydride →
appearance of pink colour on heating → presence of
steroids and triterpinoids.
Test for Coumarin glycoside
• Coumarins 2ml extract + 3ml NaOH (10%) Yellow
coloration
YPCRC 38
 Function of glycosides
• Converting toxic materials to non or less toxic.

• Transfer water insoluble substances by using monosaccharide.

• Source of energy (sugar reservoir).

• Regulation for certain functions(growth).

• Some have beautiful colours (pollenation process).

• Some glycosides have antibacterial activity, so they protect the

plants from bacteria and diseases.
YPCRC 39
 Summary
• General introduction of Glycosides

• Definition

• Chemistry & chemical classes of Glycosides

• Occurrences and distribution

• Properties

• Chemical test

• Function YPCRC 40
 References
• Pharmacognosy and Phytochemistry II by Prof.
R.R. Wadekar, Prof. Mrs. M. C Kuchekar
• Pharmacognosy and Phytochemistry – A
Comprehensive Approach by S.L. Deore S. S.
Khadabadi
• Pharmacognosy and Phytochemistry by Binod D
Rangari
• Pharmacognosy and Phytochemistry II by S.S.
Gokhale, Mrs. Aditi Kulkarni Joshi

YPCRC 41
YPCRC 42