Chemical Properties
Yellow crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from Usnea diffracta Vain.
Uses
(+)-Usnic acid has been used to study the following:
- The mechanism of its antimicrobial activity in bacterial cells.
- Its ability as an antibiofilm agent against Group A Streptococci (GAS).
- Its ability as a potent anti-virulent compound against Candida albicans.
- The mechanism of its toxic effect on hepatocytes.
- Its ability to inhibit the motility of human lung cancer cells.
Uses
Usnic Acid acts as an antibacterial and antifungal agent, and are often seen used in cosmetics and facial application chemicals.
Uses
Usnic acid is used as fragrance; preservative in deodorants; in anti ac ne formulations; antibiotic for topical application.
Definition
ChEBI: (-)-usnic acid is the (-)-enantiomer of usnic acid. It has a role as an EC 1.13.11.27 (4-hydroxyphenylpyruvate dioxygenase) inhibitor. It is a conjugate acid of a (-)-usnic acid(2-). It is an enantiomer of a (+)-usnic acid.
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Biological Activity
mic: 0.05 μg/62.5 μl to 3.1 μg/62.5 μlmicroorganisms can colonize a wide variety of medical devices, putting patients at risk for systemic and local infectious complications, including local-site infections, endocarditis, and catheter-related bloodstream infections. (+)-usniacin is a secondary lichen metabolite that possesses antimicrobial activity against various planktonic gram-positive bacteria.
in vitro
(+)-usniacin showed antimicrobial activity against the same microorganisms as that of acetone extract. among the three analogues it was the most active one having quite low mic values. furthermore, (+)-usniacin did not show any activity against a. hydrophila and b. cereus whereas (d)-usnic acid did. on the other hand, (+)-usniacin was active against y. enterocolitica whereas (d)-usnic acid was not active [1].
Purification Methods
This very weak acid is the natural form which is recrystallised from Me2CO, MeOH or *C6H6. At 25o it is soluble in H2O (<0.01%), Me2CO (0.77%), EtOAc (0.88%), MeOCH2CH2OH (0.22%) and furfural (7.32%). [Curd & Robertson J Chem Soc 894 1937, Barton & Brunn J Chem Soc 603 1953, resolution: Dean et al. J Chem Soc 1250 1953, synthesis: Barton et al. J Chem Soc 538 1956, Beilstein 18/5 V 586.]
References
[1] tay t, türk ao, yilmaz m, türk h, kivan? m. evaluation of the antimicrobial activity of the acetone extract of the lichen ramalina farinacea and its (+)-usnic acid, norstictic acid, and protocetraric acid constituents. z naturforsch c. 2004 may-jun;59(5-6):384-8.
[2] ghione m, parrello d, grasso l. usnic acid revisited, its activity on oral flora. chemioterapia. 1988 oct;7(5):302-5.
