(+)-Usnic acid, a product of secondary metabolism in lichens, has displayed a broad range of biological properties such as antitumor, antimicrobial, antiviral, anti-inflammatory, and insecticidal activities. Interested by these pharmacological activities and to tap into its potential, we herein present the synthesis and biological evaluation of new usnic acid enaminone-conjugated 1,2,3-triazoles - as antimycobacterial agents. (+)-Usnic acid was condensed with propargyl amine to give usnic acid enaminone with a terminal ethynyl moiety. It was further reacted with various azides - under copper catalysis to give triazoles - in good yields. Among the synthesized compounds, saccharin derivative proved to be the most active analogue, inhibiting () at an MIC value of 2.5 μM. Analogues and , with 3,4-difluorophenacyl and 2-acylnaphthalene units, respectively, inhibited at MIC values of 5.4 and 5.3 μM, respectively. Among the tested Gram-positive and Gram-negative bacteria, the new derivatives were active on , with compounds [3-(trifluoromethyl)phenacyl] and (N-acylmorpholinyl) showing inhibitory concentrations of 41 and 90.7 μM, respectively, while they were inactive on the other tested bacterial strains. Overall, the study presented here is useful for converting natural (+)-usnic acid into antitubercular and antibacterial agents via incorporation of enaminone and 1,2,3-triazole functionalities.
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http://dx.doi.org/10.1021/acs.jnatprod.9b00475 | DOI Listing |
Plant Physiol Biochem
December 2024
Department of Plant Biology, Pavol Jozef Šafárik University in Košice, Mánesova 1889/23, 040 01, Košice, Slovakia. Electronic address:
Allelopathy, the chemical interaction of plants by their secondary metabolites with surrounding organisms, profoundly influences their functional features. Lichens, symbiotic associations of fungi and algae and/or cyanobacteria, produce diverse secondary metabolites, among other usnic acid, which express to have potent biological activities. Mosses, i.
View Article and Find Full Text PDFBiofilm
December 2024
Department of Preventive Dentistry, School of Dentistry, Jeonbuk National University, Jeonju, Republic of Korea.
Bacterial biofilms are highly structured surface associated architecture of micro-colonies, which are strongly bonded with the exopolymeric matrix of their own synthesis. These exopolymeric substances, mainly exopolysaccharides (EPS) initially assist the bacterial adhesion and finally form a bridge over the microcolonies to protect them from environmental assaults and antimicrobial exposure. Bacterial cells in dental biofilm metabolize dietary carbohydrates and produce organic acids.
View Article and Find Full Text PDFComput Biol Chem
December 2024
Faculty of Industrial Sciences and Technology, Universiti Malaysia Pahang Al-Sultan Abdullah, Lebuhraya Persiaran Tun Khalil Yaakob, Gambang, Kuantan, Pahang 26300, Malaysia; Centre for Bio-aromatic Research, Universiti Malaysia Pahang Al-Sultan Abdullah, Lebuhraya Persiaran Tun Khalil Yaakob, Gambang, Kuantan, Pahang 26300, Malaysia. Electronic address:
Chem Biodivers
November 2024
Laboratoire des Agroressources, Biomolécules et Chimie pour l'Innovation en Santé (LABCiS), UR 22722, Université de Limoges, Limoges, France.
Lichen substances have been first described in the 1870s, and around 10 000 compounds have been isolated and characterized. Most of them have been evaluated for their activity on planktonic microorganisms (bacteria and fungi). More recently, microorganisms colonizing the lichen thallus have been isolated and identified using DNA sequencing, giving access to a wide diversity of culturable microorganisms.
View Article and Find Full Text PDFInt J Mol Sci
November 2024
Department of Medicinal Chemistry, N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. Lavrentjev Ave., 630090 Novosibirsk, Russia.
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