Friedelin

Friedelin is a natural product classified as a pentacyclic triterpene of the friedelane type. It is a C30 terpenoid that contains a ketone functional group, and it features the characteristic friedelane skeleton. The compound is highly hydrophobic and is typically isolated from plant materials rather than synthesized in the laboratory.

Natural occurrence and sources: Friedelin has been identified in a variety of plant species, often in woody tissues, bark, leaves, or resinous exudates. It has been reported as a constituent of Maytenus species, among others, illustrating its distribution across different plant lineages. The exact concentration and occurrence can vary with species and tissue type.

Chemistry and properties: As a lipophilic triterpene, friedelin is insoluble in water and dissolves in nonpolar organic solvents such as hexane, chloroform, and benzene. Isolation from plant material usually involves solvent extraction followed by chromatographic purification.

Biosynthesis: In plants, friedelin is formed biosynthetically from oxidosqualene via the action of a specific oxidosqualene cyclase enzyme known as friedelin synthase, which directs cyclization toward the friedelane framework.

Biological activity and applications: Friedelin has been studied in phytochemical and pharmacological contexts. In vitro evidence has suggested potential anti-inflammatory, antimicrobial, and cytotoxic activities, but results are variable and translational significance remains to be established. It also serves as a reference compound in triterpene chemistry and contributes to understanding plant secondary metabolism.