Usnic acid
A naturally occurring compound found in lichens
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Usnic acid is a naturally occurring dibenzofuran derivative found in several lichen species. It is known for its antimicrobial properties and has been used in traditional medicine and modern applications.
Structure and properties
Usnic acid is a yellow, crystalline substance that is soluble in organic solvents but poorly soluble in water. It has a complex structure characterized by a dibenzofuran core with additional functional groups that contribute to its biological activity.
Occurrence
Usnic acid is found in many lichen species, including Usnea, Cladonia, and Evernia. These lichens are distributed worldwide, and the concentration of usnic acid can vary depending on environmental conditions and the specific lichen species.
Biological activity
Usnic acid exhibits a range of biological activities, most notably its antimicrobial properties. It has been shown to be effective against various bacteria, fungi, and viruses. Additionally, usnic acid has been studied for its potential anti-inflammatory and antioxidant effects.
Uses
In traditional medicine, lichens containing usnic acid have been used for their purported healing properties. In modern applications, usnic acid is used in cosmetics, perfumes, and as a dietary supplement. However, its use in supplements has raised concerns due to potential hepatotoxicity.
Biosynthesis
The biosynthesis of usnic acid involves several enzymatic steps starting from simple phenolic precursors. The proposed biosynthetic pathway includes the formation of a dibenzofuran core followed by various modifications to produce the final usnic acid structure.
Safety and toxicity
While usnic acid has beneficial properties, it can also be toxic, particularly to the liver. Cases of liver damage have been reported in individuals consuming supplements containing usnic acid. Therefore, caution is advised when using products containing this compound.
Related pages
References
Usnic acid structure
Proposed biosynthesis for usnic acid
Acetoacetylation with diketene
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Contributors: Prab R. Tumpati, MD
