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At least 19 recordsLinked to original sources
PubMed1995

In vitro activities of the lichen secondary metabolites vulpinic acid, (+)-usnic acid, and (-)-usnic acid against aerobic and anaerobic microorganisms.

Secondary metabolites of different species of lichen were tested for their activities against a variety of microbial species. While gram-negative rods and fungi were not inhibited by these compounds, Staphylococcus aureus, Enterococcus faecalis, Enterococcus faecium, and some anaerobic species (Bacteroides and Clostridium species) were susceptible at the concentrations tested. Vulpinic acid generally was less active than usnic acid, regardless of its stereochemistry. The susceptibility to usnic acid was not impaired in clinical isolates of S. aureus resistant to methicillin and/or mupirocin.

Anti-Bacterial Agents↗
PubMed1995

Usnic acid and diffractaic acid as analgesic and antipyretic components of Usnea diffracta.

Diffractaic acid and usnic acid were identified as the analgesic and antipyretic components of a lichen, Usnea diffracta. Both compounds showed an analgesic effect by the acetic acid-induced writhing and tail-pressure methods in mice. Regarding the effect on normal body temperature and LPS-induced hyperthermia in mice, diffractaic acid showed a significant effect only on the former and usnic acid only on the latter.

Analgesics↗
PubMed2006

Photosynthesis and water relations in tomato plants cultivated long-term in media containing (+)-usnic acid.

The influence of (+)-usnic acid on rates of gas exchange (photosynthesis, respiration, and transpiration) in long-term cultivation of tomato plants was studied. The effect was dose-dependent. Plants grown in media containing the maximum concentration of (+)-usnic acid (30 muM) had photosynthetic and respiration rates reduced by 41% and 80%, respectively. The effect on photosynthesis rate may be the result of a multidirectional effect at various stages of this process, which at the highest usnic acid concentration underwent reduction: content of chlorophylls by 30%, carotenoids by 35%, and Hill reaction activity by 75%. Usnic acid also raises the susceptibility of chlorophyll to photodegradation. Under some conditions, transpiration was reduced by 2.1-fold in light and 3.7-fold in dark. This result was correlated with (1) an increase in the diffusive resistance of the stomata (3.1-fold in upper and 1.5-fold in lower surface of leaf), (2) a reduction of stomata density (by 60% on upper and 40% on lower surface), and (3) a 12.3-fold decrease in root hydraulic conductance.

Benzofurans↗
PubMed1997

Antimitotic effects of usnic acid on different biological systems.

Usnic acid is a biosynthesis product characteristic of several epiphytic lichens such as Evernia, Cladonia and Parmelia. Usnic acid has several interesting biological properties. It is an antibiotic and it also seems to exert an antimitotic action. It has even been postulated that usnic acid can play a role as an environmental indicator, since its concentration varies according to the presence of toxic agents. A series of tests have been run on different biological systems such as fungi, yeasts, plant cells and neoplastic human cell cultures in order to make a general evaluation of the properties of usnic acid and to highlight any analogy between its effects on phylogenetically distant organisms. The results obtained confirm some of the already known properties of usnic acid and identify concentration ranges that are active against cells from different organisms. Furthermore, at low concentrations, the acid displays a capacity to stimulate cell metabolism in some of the biological systems tested.

Adenocarcinoma↗
PubMed2006

Severe hepatotoxicity associated with use of a dietary supplement containing usnic acid.

Dietary supplements containing usnic acid are marketed for weight loss and have been associated with hepatotoxicity. The specific ingredient responsible for the hepatotoxicity is currently unknown. We describe 2 patients who developed severe hepatotoxicity within 3 months of taking a dietary supplement containing usnic acid. One patient developed fulminant hepatic failure requiring emergency liver transplantation; the other developed submassive hepatic necrosis but did not require transplantation. Thorough investigation, including histopathological examination of the liver, revealed no other cause of acute liver injury. Usnic acid hepatotoxicity should be considered as a possible etiologic factor in patients presenting with fulminant hepatic failure, especially if they have been taking dietary supplements for weight reduction.

Adult↗
PubMed2002

Usnic acid.

Since its first isolation in 1844, usnic acid [2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzo-furandione] has become the most extensively studied lichen metabolite and one of the few that is commercially available. Usnic acid is uniquely found in lichens, and is especially abundant in genera such as Alectoria, Cladonia, Usnea, Lecanora, Ramalina and Evernia. Many lichens and extracts containing usnic acid have been utilized for medicinal, perfumery, cosmetic as well as ecological applications. Usnic acid as a pure substance has been formulated in creams, toothpaste, mouthwash, deodorants and sunscreen products, in some cases as an active principle, in others as a preservative. In addition to antimicrobial activity against human and plant pathogens, usnic acid has been shown to exhibit antiviral, antiprotozoal, antiproliferative, anti-inflammatory and analgesic activity. Ecological effects, such as antigrowth, antiherbivore and anti-insect properties, have also been demonstrated. A difference in biological activity has in some cases been observed between the two enantiomeric forms of usnic acid. Recently health food supplements containing usnic acid have been promoted for use in weight reduction, with little scientific support. The emphasis of the current review is on the chemistry and biological activity of usnic acid and its derivatives in addition to rational and ecologically acceptable methods for provision of this natural compound on a large scale.

Analgesics↗
PubMed2005

[The study on skin wound healing promoting action of sodium usnic acid].

OBJECTIVE: To study the effects of sodium usnic acid on proliferation of fibroblasts and skin wound healing. METHODS: L929 fibroblasts were incubated in culture medium containing sodium usnic acid, the proliferation of fibroblasts were measured by MTT. Skin wound healing promoting action of sodium usnic acid was determined in rats. RESULTS: Sodium usnic acid does not showed proliferation-promoting activity for L929 fibroblasts, sodium usnic acid by external application accelerated healing of rat backskin wound. The wound-healing rate of sodium usnic acid was higher than that of the control group at the 2th - 12th day after treatment. CONCLUSION: Sodium usnic acid can accelerate skin wound healing, the effects was not by stimulating proliferation of fibroblasts.

Administration, Topical↗
PubMed1995

In vitro protein binding and tissue distribution of D(+) usnic acid.

In vitro protein binding of D(+) usnic acid in rabbit plasma and purified bovine serum albumin was investigated by equilibrium dialysis. The drug was highly protein bound, approximately 99.2%, and the extent of protein binding remained constant at usnic acid concentrations in the range of 1-5 micrograms/ml. The extent of binding, however, tended to decrease at low albumin concentrations and higher drug concentrations; Scatchard plot analysis indicated the existence of two classes of binding sites with association constants of 34.3 x 10(-6) and 1.43 x 10(-6) M respectively. Tissue distribution studies of usnic acid were undertaken in rats following i.p. administration. Usnic acid was well distributed into well perfused organs. The tissue/plasma ratio in lungs was high, which could be advantageous in a therapeutic agent for pulmonary tuberculosis.

Animals↗
PubMed2006

Nanoencapsulation of usnic acid: An attempt to improve antitumour activity and reduce hepatotoxicity.

Despite the recognised antiproliferative and antitumour properties of usnic acid, its therapeutic application has yet to be introduced. In fact, the high hepatotoxicity and low water solubility of usnic acid have somewhat restricted its practical use in anticancer therapy. The aim of this study was therefore to investigate the antitumour activity of usnic acid encapsulated into nanocapsules prepared with lactic co-glycolic acid polymer. Usnic acid-loaded nanocapsules were obtained using the interfacial deposition of a preformed polymer. The antitumour activity was confirmed on an ascitic tumour (Sarcoma-180) implanted in Swiss mice and estimated by means of the tumour inhibition. The results of antitumour activity confirmed that the encapsulation of usnic acid into PLGA-nanocapsules produced a 26.4% increase in tumour inhibition as compared with the standard free usnic acid treatment. Vacuolization of hepatocytes and a mild lymphocytic infiltration in portal spaces were observed in animals treated with free usnic acid. However, this hepatotoxicity was substantially reduced when animals were treated with usnic acid-loaded nanocapsules. No histological changes were noticed in the kidneys or spleen of animals treated either with usnic acid or usnic acid-loaded nanocapsules. These results suggest that nanoencapsulation may be a way of enabling usnic acid to be used in chemotherapy.

Animals↗
PubMed2002

A review on usnic acid, an interesting natural compound.

Lichens are a world-widespread consortium of fungal and photosynthetic partners. Usnic acid is one of the most common and abundant lichen metabolites, well known as an antibiotic, but also endowed with several other interesting properties. This review summarises the most relevant studies on usnic acid, focusing on a number of biological activities in different fields. On the basis of the existing literature, usnic acid seems to be an exclusive lichen product. No synthetic derivatives more effective than the natural form are known. Both the (+) and (-) enantiomers of usnic acid are effective against a large variety of Gram-positive (G+) bacterial strains, including strains from clinical isolates, irrespective of their resistant phenotype. Of particular relevance is the inhibition of growth of multi-resistant strains of Streptococcus aureus, enterococci and mycobacteria. The (+)-usnic acid enantiomer appears to be selective against Streptococcus mutans without inducing perturbing side effects on the oral saprophyte flora. On the other hand, the (-)-usnic acid enantiomer is a selective natural herbicide because of its blocking action against a specific key plant enzyme. Other recognised characteristics of usnic acid are ultraviolet absorption and preserving properties. The toxicology, the in vitro anti-inflammatory effects and the mechanism of action of usnic acid need to be investigated in greater detail in order to reach clinical trials and to allow further applications. Furthermore, more research is needed to make possible intensive lichen culture, in order to produce large quantities of lichen substances for pharmaceutical, cosmetic and agricultural purposes. Some biological aspects, i.e. the possible biological roles of usnic acid, are discussed.

Anti-Bacterial Agents↗
PubMed1965

Allergy to lichens. Allergic contact dermatitis from usnic acid produced by lichenized fungi.

Two forest workers affected with allergic contact dermatitis, which occurred only during work in forest areas, showed positive patch test reactions to lichens containing usnic acid and to isolated usnic acid. Lichens are plants composed of fungi living in symbiosis with algae. Usnic acid, one of the lichenic acids which accumulates in lichenized fungi, is a monobasic acid with dibenzofuran structure and antibiotic properties. Dibenzofuran is chemically related to furocoumarans. Lichens are plentiful in temperate zone forests and allergy to usnic acid represents some part of the "cedar-poisoning" problem in British Columbia. Geographical distribution of lichens containing usnic acid suggests that allergy to usnic acid will be found to be more common than presently recognized.

Adult↗
PubMed2001

Reversed-polarity capillary zone electrophoretic analysis of usnic acid.

A capillary zone electrophoretic (CZE) method for the determination of usnic acid is described for the first time. Usnic acid is an antibiotic substance from lichens. Due to its low solubility in water, a high content of methanol in CZE buffer is required. Because of the methanol in the buffer, the electroosmotic flow velocity was lower than the electrophoretic mobility of usnic acid. Accordingly, the use of reversed-polarity (with the anode on the detector side of the capillary) was necessary. The optimal buffer composition was 50 mM NaOH, 20 mM acetic acid and 5% water in methanol. The detection limit of UV detector at 290 nm for usnic acid in the injected extract was 3.5 mg/L and the relative standard deviation of the normalized peak area was 3.3% at 250 mg/L.

Anti-Infective Agents↗
PubMed1988

Usnic acid revisited, its activity on oral flora.

The antibacterial activity of usnic acid, the most widely distributed antibiotic among the numerous ones produced by many lichen species has been re-examined and particular attention has been devoted to the activity of optically active forms of usnic acid against Streptococcus mutans. The D(+) enantiomer was found to be more active than the L(+) form and was observed to exert a rather selective activity against S. mutans. Trials carried out in volunteers showed that mouth-rinse with D(+) usnic acid preparations exerted a selective and long lasting action against S. mutans, without substantially altering the equilibrium of normal oral bacterial flora. The adherence of S. mutans to smooth surfaces is not increased by the presence of subinhibiting concentrations of D(+) usnic acid. This is at variance with what has been observed with other antibiotics. These characteristics make D(+) usnic acid a suitable candidate for topical use in oral medicine.

Benzofurans↗
PubMed2004

Hepatotoxic effect of (+)usnic acid from Usnea siamensis Wainio in rats, isolated rat hepatocytes and isolated rat liver mitochondria.

Hepatotoxic effect of (+)usnic acid, the active constituent of Usnea siamensis Wainio was studied in rats, isolated rat hepatocytes and isolated rat liver mitochondria. In rats, after treatment with high dose of (+)usnic acid (200 mg/kg per day, i.p.) for 5 days, there was no significant change in serum transaminase activity (serum AST, ALT) while the electron micrographs showed apparent morphological damage of mitochondria and endoplasmic reticulum. (+)Usnic acid at high dose (1 mM) as well as carbon tetrachloride (CCl4, the reference hepatotoxin) induced loss of cell membrane integrity in isolated rat hepatocytes by increasing the release of cellular transaminases (AST, ALT). Increase in lipid peroxidation, decrease in glutathione (GSH) content and increase in aniline hydroxylase activity (CYP 2E1) were also found. Combination of (+)usnic acid and CCl4 showed the additive results. (+)Usnic acid (0.15-6 microM) possessed uncoupling activity in isolated rat liver mitochondria. It stimulated respiration by mitochondria respiring with glutamate plus malate or succinate as substrates and activated ATPase activity. Increasing concentration of (+)usnic acid (>6 microM) exhibited loss of respiratory control and ATP synthesis. In conclusion, hepatotoxic effect of high dose (+)usnic acid may involve its reactive metabolite(s), causing loss of integrity of membrane like structures, resulting in destruction of mitochondrial respiration and oxidative phosphorylation.

Animals↗