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== Usnic Acid ==
{{Short description|A naturally occurring compound found in lichens}}
{{Chembox
| ImageFile = Usnic_acid.svg
| ImageSize = 200px
| ImageAlt = Structural formula of usnic acid
| IUPACName = (2S)-2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzo-furandione
| OtherNames = Usninic acid
}}


Usnic acid is a natural compound that belongs to the class of depsidones. It is commonly found in lichens, which are symbiotic organisms consisting of a fungus and an alga or cyanobacterium. Usnic acid is known for its antimicrobial properties and has been used in traditional medicine for centuries.
'''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.


=== Chemical Structure ===
==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.


Usnic acid has a molecular formula of C18H16O7 and a molecular weight of 344.32 g/mol. It is composed of a dibenzofuran core structure with a carboxylic acid group and several hydroxyl groups attached to it. The compound has a yellowish color and forms needle-like crystals.
==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.


=== Natural Sources ===
==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.


Usnic acid is primarily found in various lichen species, including Usnea barbata, Usnea ceratina, and Cladonia species. These lichens are commonly found in forests, mountains, and other natural habitats. Usnic acid is synthesized by the lichen's fungal component and is believed to play a role in protecting the lichen from microbial infections.
==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]].


=== Biological Activities ===
==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.


Usnic acid exhibits a wide range of biological activities, making it a subject of interest in various fields of research. Some of its notable activities include:
[[File:Proposed_biosynthesis_for_usnic_acid.png|thumb|center|500px|Proposed biosynthesis pathway for usnic acid]]


1. Antimicrobial Activity: Usnic acid has been shown to possess strong antimicrobial properties against a broad spectrum of bacteria, fungi, and viruses. It inhibits the growth of pathogens by disrupting their cell membranes and interfering with their metabolic processes.
==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.
2. Anti-inflammatory Activity: Usnic acid has demonstrated anti-inflammatory effects by inhibiting the production of pro-inflammatory molecules in immune cells. This property makes it a potential candidate for the development of anti-inflammatory drugs.
 
3. Antioxidant Activity: Usnic acid acts as an antioxidant by scavenging free radicals and preventing oxidative damage to cells. This property may contribute to its protective effects against various diseases associated with oxidative stress.
 
4. Anticancer Activity: Preliminary studies have shown that usnic acid exhibits anticancer properties by inducing apoptosis (programmed cell death) in cancer cells. However, further research is needed to fully understand its potential in cancer treatment.
 
=== Uses ===
 
Due to its antimicrobial properties, usnic acid has been used in various applications, including:
 
1. Topical Treatments: Usnic acid is commonly used in topical creams, ointments, and lotions for the treatment of skin infections, wounds, and burns. Its antimicrobial activity helps prevent the growth of bacteria and fungi, promoting faster healing.
 
2. Oral Health Products: Usnic acid is incorporated into mouthwashes, toothpaste, and oral hygiene products due to its ability to inhibit the growth of oral pathogens. It helps maintain oral health by preventing dental caries and gum diseases.
 
3. Cosmetics: Usnic acid is used in cosmetic products, such as creams, lotions, and shampoos, for its antimicrobial and antioxidant properties. It helps protect the skin and hair from microbial infections and oxidative damage.
 
=== Safety and Precautions ===
 
While usnic acid has shown promising biological activities, it is important to note that it can be toxic if consumed in large amounts. High doses of usnic acid have been associated with liver toxicity and other adverse effects. Therefore, it is recommended to use products containing usnic acid as directed and consult a healthcare professional if any adverse reactions occur.
 
== See Also ==


==Related pages==
* [[Lichen]]
* [[Lichen]]
* [[Antimicrobial]]
* [[Antimicrobial]]
* [[Antioxidant]]
* [[Dibenzofuran]]
* [[Anti-inflammatory]]
* [[Apoptosis]]
 
== References ==


<references>
==References==
1. Li, X., et al. (2019). Usnic acid: A review of its anticancer effects and mechanisms. Frontiers in Pharmacology, 10, 1172.
{{Reflist}}
2. Ranković, B., et al. (2007). Usnic acid in lichens – a valuable secondary metabolite. Phytochemistry Reviews, 6(2-3), 287-297.
3. Singh, B., et al. (2018). Usnic acid: A potential compound targeting apoptosis for cancer therapy. Journal of Enzyme Inhibition and Medicinal Chemistry, 33(1), 846-857.
</references>


[[Category:Chemical Compounds]]
[[Category:Natural phenols]]
[[Category:Pharmacology]]
[[Category:Lichenology]]
[[Category:Natural Products]]
[[Category:Antimicrobials]]
<gallery>
File:Usnic_acid.svg|Usnic acid structure
File:Proposed_biosynthesis_for_usnic_acid.png|Proposed biosynthesis for usnic acid
File:AcetoacetylationWithDiketene.svg|Acetoacetylation with diketene
</gallery>

Latest revision as of 00:47, 18 February 2025

A naturally occurring compound found in lichens


Chemical Compound
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References

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[edit]

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[edit]

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[edit]

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[edit]

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[edit]

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.

Proposed biosynthesis pathway for usnic acid

Safety and toxicity[edit]

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[edit]

References[edit]

<references group="" responsive="1"></references>

  • Usnic acid structure
    Usnic acid structure
  • Proposed biosynthesis for usnic acid
    Proposed biosynthesis for usnic acid
  • Acetoacetylation with diketene
    Acetoacetylation with diketene
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