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Questions and Answers
What is the basic steroidal structure shared by all cardiac glycosides?
What is the basic steroidal structure shared by all cardiac glycosides?
Cyclopentaphenanthrene
The active ingredient found in the scientific name Digitalis purpurea is called __________.
The active ingredient found in the scientific name Digitalis purpurea is called __________.
digoxin
What role do cardiac glycosides play in heart function, and how do they exert this effect on the sodium-potassium ATPase pump?
What role do cardiac glycosides play in heart function, and how do they exert this effect on the sodium-potassium ATPase pump?
Cardiac glycosides increase the output force of the heart and its contraction rate by inhibiting the sodium-potassium ATPase pump, leading to increased intracellular calcium levels.
Describe the structural components that make up the cyclopentaphenanthrene nucleus in cardiac glycosides.
Describe the structural components that make up the cyclopentaphenanthrene nucleus in cardiac glycosides.
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Differentiate between cardenolides and bufadienolides based on their structures and provide an example of each.
Differentiate between cardenolides and bufadienolides based on their structures and provide an example of each.
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What is the significance of the lactone ring's saturation at the C-17 position in cardiac glycosides?
What is the significance of the lactone ring's saturation at the C-17 position in cardiac glycosides?
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Identify the sugar part associated with cardiac glycosides and explain its role in their pharmacological effectiveness.
Identify the sugar part associated with cardiac glycosides and explain its role in their pharmacological effectiveness.
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Study Notes
Cardiac Glycosides
- Cardiac glycosides are organic compounds that increase the force and rate of heart contractions by affecting the sodium-potassium ATPase pump.
- They are steroidal glycosides used to treat heart failure and cardiac rhythm disorders.
Structure
- All cardiac glycosides contain the cyclopentaphenanthrene structure, a tetracyclic aromatic structure.
- Cyclopentaphenanthrene consists of three fused benzene rings (phenanthrene) and a five-membered cyclopentane ring.
Groups
- Cardiac glycosides are divided into two groups: Cardenolides and Bufadienolides.
Cardenolides
- Contain a five-membered unsaturated lactone ring at the C-17 position of the steroid nucleus.
- Examples include Digoxine from foxglove and Oliandrin from oleander (rosebay).
Bufadienolides
- Contain a six-membered lactone ring at the C-17 position of the steroid nucleus.
- Examples include scillarenin, obtained from Squill (rodenticide).
Key Features
- C-17 Position: Alpha or beta unsaturated lactone ring.
- C-14 Position: Hydroxyl group (OH).
-
Ring Junctions:
- AB Ring: Cis
- BC Ring: Trans
- CD Ring: Cis
- C-3 Beta Position: Sugar part (glucose - rhamnose - digitoxose).
Examples
-
Digitalis purpurea (Foxglove):
- Active ingredient: Digoxin
- Family: Plantaginaceae
-
Nerium oleander (Oleander):
- Active ingredient: Oleandrin
- Family: Apocynaceae
Cardiac Glycosides
- Cardiac glycosides are organic compounds that enhance the heart's pumping force and contraction rate.
- They achieve this by influencing the cellular sodium-potassium ATPase pump.
- This class of drugs is essential for treating heart failure and cardiac rhythm problems.
Chemical Structure:
- All cardiac glycosides share the basic steroidal nucleus, cyclopentaphenanthrene, a tetracyclic aromatic structure.
- Cyclopentaphenanthrene comprises two parts:
- Three fused benzene rings (phenanthrene)
- Five-membered cyclopentane ring
Classification:
- Cardiac glycosides are categorized into two groups:
- Cardenolides (23 Carbon atoms):
- Contain a 5-membered unsaturated lactone ring at the C-17 position of the steroid nucleus.
- Examples include digoxin from foxglove and oleandrin from oleander or rosebay.
- Bufadienolides (24 Carbon atoms):
- Contain a 6-membered lactone ring at the C-17 position of the steroid nucleus.
- Example includes scillarenin, sourced from Squill (rodenticide).
- Cardenolides (23 Carbon atoms):
Key Structural Features:
- At the C-17 position, there is an alpha or beta unsaturated lactone ring.
- At the C-14 position, there is an OH (hydroxyl) group.
- The ring junctions are configured as follows:
- AB ring: cis
- BC ring: trans
- CD ring: cis
- At the C-3 beta position, there is a sugar part (glucose - rhamnose - digitoxose).
Examples of Cardiac Glycosides:
-
Digitalis purpurea (Foxglove):
- Active ingredient: digoxin.
- Family: Plantaginaceae.
-
Nerium oleander (Oleander):
- Active ingredient: oleandrin.
- Family: Apocynaceae.
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Description
Explore the fascinating world of cardiac glycosides, organic compounds crucial for treating heart failure and rhythm disorders. Learn about their unique cyclopentaphenanthrene structure and the two main groups: Cardenolides and Bufadienolides. This quiz will test your understanding of their roles and chemical characteristics.
