(+)-Usnic acid enamines with remarkable cicatrizing properties

Bruno, Michela; Trucchi, Beatrice; Burlando, Bruno; Ranzato, Elia; Martinotti, Simona; Akkol, Esra Küpeli; Süntar, İpek; Keleş, Hikmet; Verotta, Luisellá

doi:10.1016/j.bmc.2013.01.045

Cited by 45 publications

(40 citation statements)

References 27 publications

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“…Furthermore, we synthesized conjugates obtained by addition of aromatic and heterocyclic hydrazines and hydrazides ( PS1 , PS10 , PS17 , PS18 , PS19 ) (Figure ). Usnic acid underwent addition of nitrogen nucleophilic systems in neutral or basic conditions, as described in detail previously . The synthesis and antitubercular activity of conjugate PS19 has been recently described elsewhere …”

Section: Resultsmentioning

confidence: 99%

“…The role of the acidic enol portion of usnic acid in its intrinsic antimycobacterial activity was confirmed through the synthesis of enaminousnic (BT51), obtained by refluxing usnic acid in ammonia solution that shows no activity (MIC > 64 mg/L) on all mycobacteria strains.…”

Section: Discussionmentioning

confidence: 96%

“… while for compounds PS2 , PS6 , PS8 , PS9 , enaminousnic ( BT51 ) are reported in Ref. . Detailed synthesis of selected compounds ( PS3 , PS17 , and PS19 ) are here reported.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis and antimycobacterial activity of (+)‐usnic acid conjugates

Cirillo

Borroni

Festoso

et al. 2018

Archiv der Pharmazie

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New therapeutics are urgently needed to fight tuberculosis and mycobacteria-related diseases that are a major health hazard especially in poor countries. Natural products have been the source of important antitubercular drugs in the past and still need to receive attention as a potent reservoir of chemical structures. Fifteen known and two new (+)-usnic acid (a benzofurandione formerly isolated from lichens) enamines and hydrazones are here described and tested against sensitive and multidrug-resistant strains of mycobacteria. Among several (+)-usnic acid conjugates, PS14 and PS18 showed potent activity against both susceptible and resistant Mycobacterium tuberculosis strains (MIC values of 1-32 and 2-32 mg/L, respectively) comparable with MIC of other antitubercular drugs already in use for tuberculosis treatment.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 96%

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Synthesis and antimycobacterial activity of (+)‐usnic acid conjugates

Cirillo

Borroni

Festoso

et al. 2018

Archiv der Pharmazie

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“…It should be emphasized that CUE is less toxic and at the same time its antibacterial activity is stronger than pure (+)-UA, used, e.g. as an antibacterial agent in topical formulations (Bruno et al, 2013;Francolini et al, 2018). The biosynthesis potential of C. uncialis and other lichens is still poorly explored due to the lack of any experimental evidence for definite linking biosynthetic gene clusters with secondary metabolites.…”

Section: Discussionmentioning

confidence: 99%

Cladonia uncialis as a valuable raw material of biosynthetic compounds against clinical strains of bacteria and fungi

et al. 2019

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Cladonia uncialis is a lichen species with confirmed antibacterial activity and whose genome has been recently sequenced, enabling first attempts in its functional characterization. In this work, we investigated activity of the C. uncialis acetone extract (CUE) and usnic acid (UA) enantiomers against ten clinical microbial strains causing skin infections. The results showed that CUE, containing (–)-UA and squamatic acid, assayed at the same concentrations as UA, was noticeably more active than (–)-UA alone, in its pure form. The studied CUE displayed an activity that was comparable to that of (+)-UA observed for Staphylococcus epidermidis and Enterococcus faecium (18-24 mm zone of growth inhibition), but did not display any activity against fungal strains. The CUE demonstrated low cytotoxicity against HaCaT cells, in comparison to UA enantiomers, which is important for its therapeutic use. Results of the antioxidant assay (DPPH) indicated low antioxidant activity (IC50>200 µg/mL) of CUE, while the total phenolic content was 70.36 mg Gallic Acid Equivalent/g of the dry extract.

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“…It also can be used for treatment of human leg and loin injuries, bone fractures and female disease (Aalto‐Korte, Lauerma, & Alanko, ; Guo et al, ; Hager, Brunauer, Turk, & Stocker‐Worgotter, ), and ulcers (Cabanillas, Fernandez‐Redondo, & Toribio, ; Halici et al, ). Modern pharmacological studies have confirmed that Usnea plants and bioactive secondary metabolites exert a wide variety of biological functions, including antibacterial and antimycobacterial, especially to the tubercle bacillus and Gram‐positive bacteria (Honda et al, ; Ramos & Almeida, ), antipyretic, analgesic (Okuyama, Umeyama, Yamazaki, Kinoshita, & Yamamoto, ), anti‐inflammatory (Vijayakumar et al, ), antiprotozoal, apoptosis‐inducing and antitumour (Backorova et al, ; Singh, Nambiar, Kale, & Singh, ), antiviral (Shtro et al, ; Sokolov et al, ), wound healing promotion (Bruno et al, ; Burlando et al, ), photoprotective activity (Lohezic‐Le, Legouin, Couteau, Boustie, & Coiffard, ), antioxidant enzyme activity and mucosal damage (Bayir et al, ; Halici et al, ; Rabelo et al, ; Vijayakumar et al, ).…”

Section: Introductionmentioning

confidence: 99%

Simultaneous determination of usnic, diffractaic, evernic and barbatic acids in rat plasma by ultra‐high‐performance liquid chromatography–quadrupole exactive Orbitrap mass spectrometry and its application to pharmacokinetic studies

Wang

Yang

Cheng

et al. 2017

Biomedical Chromatography

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Usnea longissima Ach. (Usnea) is used in pharmaceuticals, food and cosmetics. Evernic acid (EA), barbatic acid (BA), diffractaic acid (DA) and usnic acid (UA) are the most typical ingredients in U. longissima and exert a wide variety of biological functions. The study aimed to develop a sensitive method for simultaneous analysis of EA, BA, DA and UA in rat plasma and was applied to pharmacokinetic studies after consumption of UA and ethanol extract from U. longissima (UE). The samples were separated on a BEH C column by gradient elution with 0.5% formic acid in water and in methanol. The relative molecular masses of analytes were obtained in full-scan range from 50.0 to 750.0 m/z under negative ionization mode by UPLC-Q-Exactive Orbitrap MS. All validation parameters, such as lower limit of quantitation, linearity, specificity, precision, accuracy, extraction recovery, matrix effect and stability, were within acceptable ranges and the method was appropriate for biological specimen analysis. The pharmacokinetic results indicated that the absolute bioavailabilities of UA after oral administration of UA and UE reached 69.2 and 146.9%, respectively. Compared with UA in UE, the relative bioavailability of DA, BA and EA reached 103.7, 10.4 and 0.7% after oral administration of UE.

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(+)-Usnic acid enamines with remarkable cicatrizing properties

Cited by 45 publications

References 27 publications

Synthesis and antimycobacterial activity of (+)‐usnic acid conjugates

Synthesis and antimycobacterial activity of (+)‐usnic acid conjugates

Cladonia uncialis as a valuable raw material of biosynthetic compounds against clinical strains of bacteria and fungi

Simultaneous determination of usnic, diffractaic, evernic and barbatic acids in rat plasma by ultra‐high‐performance liquid chromatography–quadrupole exactive Orbitrap mass spectrometry and its application to pharmacokinetic studies

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