Simple Indolizidine and Quinolizidine Alkaloids

Area of Science:

• Natural Product Chemistry
• Organic Chemistry
• Medicinal Chemistry

Background:

• Indolizidine and quinolizidine alkaloids are bicyclic nitrogen-containing compounds with diverse biological activities.
• Previous reviews have covered these alkaloids, necessitating an update on recent discoveries and synthetic advancements.

Purpose of the Study:

• To provide a comprehensive update on simple indolizidine and quinolizidine alkaloids published between mid-1999 and the end of 2013.
• To emphasize the total synthesis of these alkaloids alongside their isolation, characterization, and biological activities.

Main Methods:

• Literature review of scientific publications from mid-1999 to end of 2013.
• Compilation and analysis of data on isolation, characterization, biological activity, and total synthesis of indolizidine and quinolizidine alkaloids.
• Categorization of alkaloids based on their natural sources (fungal, microbial, plant, animal, marine).

Main Results:

• Detailed overview of alkaloids from fungal/microbial sources (e.g., slaframine, cyclizidine) and iminosugar alkaloids (e.g., swainsonine, castanospermine).
• Coverage of plant-derived alkaloids, including those with alkyl, alkenyl, aryl, and heteroaryl substituents, and alkaloids from the lupin family.
• Inclusion of alkaloids from ants, mites, amphibians, and marine organisms, discussing the dietary hypothesis for amphibian metabolites.

Conclusions:

• Significant progress has been made in the total synthesis and understanding of the biological roles of simple indolizidine and quinolizidine alkaloids.
• The diversity of these alkaloids across various natural sources underscores their importance in natural product chemistry and drug discovery.