Ailanthones

Ailanthones are a group of natural products classified as quassinoids, produced by the tree of heaven (Ailanthus altissima) and other members of the Simaroubaceae family. They are highly oxygenated, degraded triterpenoids that belong to the quassinoid family and are typically lactone-containing polycyclic compounds. The name derives from the plant genus Ailanthus.

Natural occurrence: Ailanthones are found in various parts of the plant, including bark, leaves, and seeds. They are thought to serve as chemical defenses against herbivores and pathogens, and can be released into the environment through plant tissues.

Biological activity: Ailanthones exhibit a range of bioactivities in laboratory studies. They have shown cytotoxic effects against several cancer cell lines, as well as antimicrobial, antifungal, and anti-inflammatory properties. Some compounds in the family also display insect antifeedant activity. The proposed mechanisms vary by compound and may involve interference with protein synthesis or cellular signaling, but precise actions are not fully understood.

Chemistry and synthesis: Compounds within the ailanthone group vary in oxidation pattern and substituents but share the characteristic quassinoid lactone framework. They have been the subject of natural product isolation, structure elucidation, and synthetic modification to explore structure–activity relationships.

Applications and considerations: While certain ailanthones and derivatives have attracted interest as potential anticancer leads, none have become approved medicines. Their toxicity to non-target organisms and the complexity of synthesis present challenges for development. They are primarily of interest to researchers in natural products chemistry and pharmacology.