title: Sesqui- and triterpenoids from the liverwort Lepidozia chordulifera inhibitors of bacterial biofilm and elastase activity of human pathogenic bacteria.
abstract: Five dammarane-type triterpenoids, five pentacyclic triterpenoids (three of them carrying a carboxylic acid group), and two aromadendrane-type sesquiterpenoids were isolated from an Argentinian collection of the liverwort Lepidozia chordulifera. Compounds were characterized by comparison of their spectral data with those previously reported and tested in their ability to control bacterial growth, biofilm formation, bacterial Quorum Sensing process (QS), and elastase activity of Pseudomonas aeruginosa, as well as bacterial growth and biofilm formation of Staphylococcus aureus. The key role played by biofilm and elastase activity in bacterial virulence make them a potential target for the development of antibacterial agents. The aromadendrane-type sesquiterpenoid viridiflorol was the most potent biofilm formation inhibitor, producing 60% inhibition in P. aeruginosa and 40% in S. aureus at 50µg/ml. Ursolic and betulinic acids (two of the pentacyclic triterpenoids isolated) were able to reduce 96 and 92% the elastase activity of P. aeruginosa at 50µg/ml, respectively. Among the analyzed triterpenoids, those that carry a dammarane skeleton were the most potent inhibitors of the P. aeruginosa biofilm formation and were active against both P. aeruginosa and S. aureus. Subsequently, a computer-assisted study of the triterpenoid compounds was carried out for a better understanding of the structure-activity relationships.
authors: INQUINOA-CONICET, Ayacucho 471, 4000 Tucumán, Argentina; Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán (UNT), Ayacucho 471, 4000 Tucumán, Argentina. Electronic address: mgilabert@fbqf.unt.edu.ar.
authors: M
authors: M
authors: Gilabert
authors: INQUINOA-CONICET, Ayacucho 471, 4000 Tucumán, Argentina.
authors: K
authors: K
authors: Marcinkevicius
authors: Facultad de Química, Bioquímica y Farmacia, Universidad Nacional de San Luís (UNSL), Ejército de Los Andes 950, 5700 San Luis, Argentina.
authors: S
authors: S
authors: Andujar
authors: Facultad de Ciencias Naturales e Instituto Miguel Lillo, Universidad Nacional de Tucumán, Miguel Lillo 251, Tucumán 4000, Argentina.
authors: M
authors: M
authors: Schiavone
authors: INQUINOA-CONICET, Ayacucho 471, 4000 Tucumán, Argentina; Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán (UNT), Ayacucho 471, 4000 Tucumán, Argentina.
authors: M E
authors: ME
authors: Arena
authors: Facultad de Bioquímica, Química y Farmacia, Universidad Nacional de Tucumán (UNT), Ayacucho 471, 4000 Tucumán, Argentina.
authors: A
authors: A
authors: Bardón
mesh_terms: D018441:Biofilms / Q000187:drug effects*; D004791:Enzyme Inhibitors / Q000494:pharmacology; D035926:Hepatophyta / Q000737:chemistry*; D015394:Molecular Structure; D010196:Pancreatic Elastase / Q000037:antagonists & inhibitors; D053978:Pentacyclic Triterpenes; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000201:enzymology; D053038:Quorum Sensing / Q000187:drug effects; D012717:Sesquiterpenes / Q000302:isolation & purification / Q000494:pharmacology*; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000494:pharmacology*; D014315:Triterpenes / Q000302:isolation & purification / Q000494:pharmacology*; D000094062:Betulinic Acid; D000097245:Ursolic Acid
chemical_list: D004791:Enzyme Inhibitors; D010196:Pancreatic Elastase; D053978:Pentacyclic Triterpenes; D012717:Sesquiterpenes; D013729:Terpenes; D014315:Triterpenes; D000094062:Betulinic Acid; D000097245:Ursolic Acid; C552080:viridiflorol
keywords: Biofilm; Elastase; Lepidozia chordulifera; Pseudomonas aeruginosa; Staphylococcus aureus