TOPIC-CARDIAC GLYCOSIDE

PRESENTED BY-
SOURAV DAS
B-PHARM,3RD YEAR,6TH SEMESTER
STUDENT ID-B16006
REGESTRATION NO.-161740210057 OF 2016-17
Roll No.-17401916013
NETAJI SUBHAS CHANDRA BOSE INSTITUTE OF PHARMACY
CONTENTS

• INTRODUCTION
• CLASSIFICATION
• STEROIDAL GLYCOSIDES OR CARDIAC GLYCOSIDES
– CHEMISTRY
– IDENTIFICATION TEST
– STEROIDAL GLYCOSIDE CONTAINING CRUDE DRUGS
• DIGITALIS
– CHEMICAL CONSTITUENT
– MECHANISM OF ACTION
• REFERENCES
INTRODUCTION
• Glycosides may be defined as
– A organic compound obtained from plant or animal sources
– On enzymatic or acid hydrolysis give
• One or more sugar moieties called GLYCONE
– FACILITATES ABSORPTION
• Along with non-sugar moiety called AGLYCONE or GENIN
– .EXHIBIT THERAPEUTIC PROPERTIES

• Chemicaly,they are
– Acetayls or sugar ethers
– Formed by interaction of hydroxyl group each of non-sugar and sugar moieties.
• The linkage between glycone and alycone is called GLYCOSIDIC LINKAGE.
• The sugars involved
– Most commonly β-D-glucose
– Galactose
– Rhamnose
– Digitoxose
– Cymarose
CLASSIFICATION
• According to chemical nature of aglycone moiety,glycosides are grouped
into
– Anthraquinone or anthracene glycosides
– Sterols or cardiac glycosides
– Saponin glycosides
– Cyanogenetic or cyanophoric glycosides
– Isothiocynate glycosides
– Flavonoid Flavonol glycosids
– Coumarins and Furanocoumaringlycosides
– Aldehyde glycosides
– Phenol glycosides
– Steroidal glycolkaloids
– Glycosidal bitters or miscellaneous glycosides
STEROIDAL GLYCOSIDES
OR
CARDIAC GLYCOSIDES
CHEMISTRY
• The aglycone part of cardiac glycoside is steroidal moiety

FIVE
MEMBERED SIX
LACTONE RING MEMBERED
LACTONE RING

CARDENOLIDE BUFADIENOLIDE
• Types of sugars have been reported-
– Glucose,Rhamnose,Digitoxose,Digitalose etc.
• The occurrence of cardenolides from nature is quite high
compared to bufadinolides
 IDENTIFICATION TEST
• KEDDE’S TEST
MAKE
EXTRACT WITH
CHLOROFORM EVAPORATE TO 1 DROP OF 90% ALCOHOL ALKALINE
DRUG WITH
DRYNESS 2DROPS OF 2%
3,5-DINITRO BENZOIC 20%SODIUUM
ACID
HYDROXIDE
SOLUTION

PURPLE
COLOUR
• KELLER-KILLIANI TEST ADD 0.5 ML
EXTRACT WITH 0.4 ML GLACIAL ACETIC
CHLOROFORM EVAPORATE TO ACID
OF
DRUG CONCENTRAT
DRYNESS TRACE AMOUNT OF
FERRIC CHLORIDE ED
SULPHURIC
ACID

ACID
LAYER
SHOWS
BLUE
COLOUR
• LEGAL’S TEST

ALKALINE SODIUM
TEST SOLUTION PYRIDINE
NITROPRUSIDE BLOOD RED
SOLUTION COLOUR

• BALJET’S TEST

TEST SOLUTION PICRIC ACID ORANGE

COLOUR
 STEROIDAL GLYCOSIDE
CONTAINING CRUDE DRUGS

NAME OF DRUG BIOLOGICAL ACTIVE USES

SOURCE CONSTITUENTS
DIGITALIS DRIED LEAVES OF DIGITALIS PURPUREA GLYCOSIDE A & CARDIOTONIC
PURPUREA, B,DIGITOXIN
SCROPHULARIACEAE

EUROPEAN SQUILL DRIED SLICED BULBS OF SCILLAREN A & B CARDIOTONIC

URGINEA MARITIMA,LILIACEAE

INDIAN SQUILL DIGITALIS

DRIED SLICED BULBS OF SCILLAREN A & B CARDIOTONIC
URGINEA INDICA,LILIACEAE

OUABAIN DRIED SEEDS OF OUABAIN CARDIOTONIC

STROPHANTHUS
GRATUS,APOCYNACEAE
STROPHANTHUS DRIED RIP SEEDS OF STROPHANTHIDIN CARDIOTONIC
STROPHANTHUS
KOMBE,APOCYNACEAE

THEVETIA DRIED SEEDS OF THEVETIA THEVETIN CARDIOTONIC

NERIFOLIA,APOCYNACEAE
 CHEMICAL CONSTITUENT
DIGITALIS PURPUREA

PURPUREA GLYCOSIDE-A PURPUREA GLYCOSIDE-B

ENZYMATIC HYDROLYSIS ENZYMATIC HYDROLYSIS

DIGITOXIN GITOXIN
(-3 DIGITOXOSE) (-3 DIGITOXOSE)

DIGITOXIGENIN DIGOXIGENIN GITOXIGENIN

(-3 DIGITOXOSE) (-3 DIGITOXOSE) (-3 DIGITOXOSE)

DIGITOXIN DIGOXIN GITOXIN

(-ACETYL) (-GLUCOSE)
(-ACETYL) (-GLUCOSE) (-ACETYL) (-GLUCOSE)

PURPUREA GLYCOSIDE-A DEACETYL LANATOSIDE-C PURPUREA GLYCOSIDE-B

ACETYLDIGITOXIN ACETYLDIGOXIN ACETYLGITOXIN
(-ACETYL) (-GLUCOSE) (-ACETYL) (-GLUCOSE) (-ACETYL) (-GLUCOSE)

LANATOSIDE-A LANATOSIDE-C LANATOSIDE-B

DIGITALIS LANATA
STRUCTURES

DIGITOXIN DIGOXIN

DIGITOXIGENIN DIGOXIGENIN
MECHANISM OF ACTION
REFERENCES

• PHARMACOGNOSY;50TH EDITION;BY C.K.KOKATE,A.P.PUROHIT ,

S.B.GOKHLE;NIRALI PRAKASHAN;PAGE NO-9.1-9.5 & 9.30-9.38

• ESSENTIAL MEDICAL PHARMACOLOGY;8TH EDITION;BY-KD

TRIPATHI;JAYPEE BROTHERS MEDICAL PUBLISHERS;PAGE NO-556-559

• GOODMAN & GILMAN’S THE PHARMACOLOGICALBASIS OF

THERAPEUTICS;12TH EDITION;BY-LAURENCE BRUNTON,BRUCE
CHABNER,BJORN KNOLLAMAN;THE McGraw-Hill Companies;PAGE N0-
817-827