Quinolizidine-Type Alkaloids: Chemodiversity, Occurrence, and Bioactivity.

Quinolizidine alkaloids (QAs) are nitrogen-containing compounds produced naturally as specialized metabolites distributed in plants and animals (e.g., frogs, sponges). The present review compiles the available information on the chemical diversity and biological activity of QAs reported during the last three decades. So far, 397 QAs have been isolated, gathering 20 different representative classes, including the most common such as matrine (13.6%), lupanine (9.8%), anagyrine (4.0%), sparteine (5.3%), cytisine (6.5%), tetrahydrocytisine (4.3%), lupinine (12.1%), macrocyclic bisquinolizidine (9.3%), biphenylquinolizidine lactone (7.1%), dimeric (7.1%), and other less known QAs (20.9%), which include several structural patterns of QAs. A detailed survey of the reported information about the bioactivities of these compounds indicated their potential as cytotoxic, antiviral, antimicrobial, insecticidal, anti-inflammatory, antimalarial, and antiacetylcholinesterase compounds, involving favorable putative drug-likeness scores. In this regard, research progress on the structural and biological/pharmacological diversity of QAs requires further studies oriented on expanding the chemical space to find bioactive scaffolds based on QAs for pharmacological and agrochemical applications.