Cardiac Glycosides – PST05210 Basic Pharmacognosy

NTA Level 5 • Semester 2 • PST05210

Cardiac Glycosides

Basic Pharmacognosy • Source Session/Topic 28
Full source-text version: all educational wording from the extracted learning source is retained; only presenter/tutor metadata and web-layout noise are removed, while formatting is improved for readability.

Session 28: Cardiac Glycosides

Total Session Time: 120 minutes

Prerequisites

• None

Learning Tasks

By the end of this session students are expected to be able to:

• Define cardiac glycosides
• List properties of cardiac glycosides
• Mention natural sources of cardiac glycosides
• Explain mechanisms of action
• Differentiate types of cardiac glycosides
• Explain chemical tests for cardiac glycosides
• Mention general uses of cardiac glycoside

Resources Needed:

• Flip charts, marker pens, and masking tape
• Black/white board and chalk/whiteboard markers
• LCD Projector and Lapatop

SESSION OVERVIEW

|Step |Time |Activity/ |Content |

| | |Method | |

|1 |5 minutes |Presentation |Introduction, Learning Objectives |

|2 |30 minutes |Presentation |Properties of Cardiac Glycosides |

|3 |60 minutes |Presentation |Sources, Constituents and Uses of |

| | | |Selected Cardiac Glycosides |

|4 |15 minutes |Presentation |Mechanism of Action for Cardiac |

| | | |Glycosides |

|5 |5 minutes |Presentation |Key Points |

|6 |5 minutes |Presentation |Evaluation |

SESSION CONTENTS

STEP 1: Presentation of Session Title and Learning Tasks (5 minutes)

READ or ASK students to read the learning tasks and clarify

ASK students if they have any questions before continuing.

STEP 2: Properties of Cardiac Glycosides (30 minutes)

• Cardiac glycosides are a group of glycosides with powerful action on

cardiac muscles (positive ionotropic effect on the heart)

• Cardiac glycosides are also made up of aglycone and glycone moities
• The Glycone part

o consists of one or more monosaccharide units

o contains a steroid nucleus and a lactone ring

• The Aglycone part

o has steroidal nucleus

o is always attached at C-3 position of aglycone part

• There are two groups of cardiac glycosides;

o Cardenolides

▪ The cardenolides have an unsaturated butyrolactone ring –a five
membered-ring e.g. strophanthus

o Bufadienolides

▪ In this group the lactone ring is a 6 membered (pyrrone) ring
▪ These are obtained from animal sources e.g. Bufadieonolides

from toads

• Characteristics of Cardiac Glycosides;

o Amorphous

o Odorless

o Bitter tasting

o Soluble in water

o Insoluble in organic solvents

o Very toxic compounds

• Chemical tests for cardiac glycosides

o Keller Kilian test

▪ Cardiac glycoside + CH3COOH + H2SO4 + FeCl3, produces brown

colour

o Legal test

▪ Cardiac glycoside + pyridine Sodium Nitroprusside, produces

red to pink colour

STEP 3: Sources, Constituents and Uses of Selected Cardiac Glycosides (60

minutes)

• Digitalis

o Definition

▪ Digitalis consists of dried leaves of Digitalis lanata or Digitalis

purpurea (common name purple fox glove), family Scrophulariaceae

▪ Digitalis – finger-like corolla
▪ Purpurea – purple colour

o Constituents

▪ D. purpurea produces primary glycosides
• Purpurea glycoside A
• Purpurea glycoside B
• Glucogitaloxin
▪ On drying, enzyme degradation taken place with the loss of the

terminal glucose to produce;

• Digitoxin from purpurea glycoside A
• Gitoxin from purpurea glycoside B
• Gitaloxin

o D. lanata produces

▪ Digoxin
▪ Lanatosides A, B and C
• During drying: acetyl terminal sugar can be lost
• Deacetylation produces primary glycosides as those produced

by Digitalis purpurea

• Lanatoside A produces Purpurea glycoside A
• Lanatoside B produces Purpurea glycoside B
• Lanatoside C produces Deslanoside C/ Deacetyllanatoside

o Uses of digitalis

▪ Digitalis glycosides are used for the treatment of;
• Congestive Heart Failure (CHF)
• Arrhythmias
• Atrial fibrillations
• Squill

o Definition

▪ Squill consists of the dried sliced bulbs of Urgenea maritima, from

which the membrenous outer scales have been removed (family

Liliaceae)

▪ The common name for squill is “sea onion”
▪ There are two types of squill; red squill and white squill

o Constituents

▪ Squill contains the glycosides;
• Scillaren A

o Which is crystalline in form

• Scillaren B

o An amorphous mixture of glycosides

• The red squill contains Scillirosides in addition to the

other glycosides

o Uses

▪ White squill
• As cardiotonic drugs
• As diuretics agents
• In small dose –as expectorant agents
• In large dose –as emetic agents
▪ Red squill
• Used as a rodenticide (due to Scillirosides)
• Strophanthus

o Definition

▪ Consist of the dried ripe seed of Strophanthus kombe/strophanthus

hispidus, family apocynaceae

o Constituents

▪ Mixture of glycosides
• K-strophanithin, erysimoside, K strophanthoside and

cymarin

• Fixed oils, resins and mucilage are also present
• K-strophanthosides;

o Composed of the genin strophanthidin

o Coupled to a trissaccharide with cymarose, β-glucose

and α-glucose

o Are short-acting cardiac glycosides

STEP 4: Mechanism of Action for Cardiac Glycosides (15 minutes)

• Cardiac glycosides act by;

o Inhibition of Na+/K+ ATPase of the cardiac cells, which increases the

intracellular Na+ ions levels

o The increased Na+ ion levels within the cardiac cells inhibits the

Na+/Ca2+ exchanger, this in turn, results in increased concentrations

of Ca2+ within the cardiac cells

o The increased intracellular Ca2+ increases contractile force of the

cardiac muscles

[pic]

STEP 5: Key Points (5 minutes)

• Cardiac glycosides are glycosides with powerful positive inotropic action

on cardiac muscles

• Digitalis consists of dried leaves of Digitalis lanata or Digitalis

purpurea

• Digoxin is obtained from Digitalis lanata
• Digitalis glycosides are used for the treatment of heart conditions

including congestive heart failure (CHF), arrhythmias and atrial

fibrillations

STEP 10: Evaluation (5 minutes)

• What is the source of digoxin?
• What is the main use of digoxin?
• What is strophanthus?

References

Trease, G. E., Evans, W. C., & Evans, D. (2009). Trease and Evans

pharmacognosy. London: Saunders.

Joanne Barnes et al (2002), Herbal medicines 3rd Edition: Pharmaceutical

Press

Wallis, T. E. (2005). Textbook of pharmacognosy. New Delhi: CBS.

Robbers, J. E., Speedie, M. K., Tyler, V. E., & Tyler, V. E. (1996).

Pharmacognosy and pharmacobiotechnology. Baltimore: Williams &

Wilkins.

Heinrich, M., Kinghorn, A. D., Maizels, D., Gibbons, S., & Phillipson, J.

D. (2012). Fundamentals of pharmacognosy and phytotherapy. Edinburgh:

Churchill Livingstone/Elsevier.

.

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