Trilactones

Trilactones are chemical compounds defined by the presence of three lactone rings within a single molecule. They are a subset of lactones and may feature three ester linkages arranged in various ways, including fused or spiro configurations, yielding either macrocyclic or polycyclic skeletons. The term is used to describe several distinct natural products that share the three-lactone motif rather than a single uniform scaffold.

Structural diversity is a hallmark of trilactones. Individual members can differ in ring size, the arrangement of the lactone units, and the pattern of substituents and stereochemistry. Because the three lactone rings can be connected in multiple ways, trilactones exhibit a range of three-dimensional shapes and chemical properties, which in turn influence their reactivity and biological activity.

Occurrence and biosynthesis are also variable. Trilactones have been reported from a variety of natural sources, including fungi, plants, and marine organisms. In nature, they are often formed through polyketide-type biosynthetic pathways, with enzymatic steps that promote ring formation and lactonization. Their chemical stability can be sensitive to hydrolysis and ring-opening, depending on ring strain and substituent effects.

Biological activity and applications vary by compound. Many trilactones have attracted interest for potential antimicrobial, antifungal, cytotoxic, or other bioactivities, and some have served as lead structures in drug discovery. Because trilactones describe a motif rather than a single compound class, research emphasizes the specific core, substituents, and three-dimensional conformation of each molecule.