Oakmoss is a natural fragrance ingredient exhibiting highly specific, potent antibacterial activity against Legionella pneumophila, a causative agent of severe water-bone pneumonia. In the present ...study, the antibacterial activity of individual compounds isolated from oakmoss was investigated against L. pneumophila and other Legionella spp. A total of 18 known compounds and two minor novel compounds (i.e., 3-methoxy-5-methylphenyl-2,4-dihydroxy-6-methylbenzoate (compound 9) and 8-(2,4-dihydroxy-6-(2-oxoheptyl)-phenoxy)-6-hydroxy-3-pentyl-1H-isochromen-1-one (compound 20)) were purified from oakmoss. The minimum inhibitory concentrations (MICs) against clinical and environmental isolates of L. pneumophila, L. bozemanii, L. micdadei, L. longbeachae, and L. dumoffii for 11 of the 20 compounds were less than 100 µg/mL (range 0.8-64.0 µg/mL). Novel compounds 9 and 20 exhibited potent antibacterial activity against L. pneumophila strains (MIC ranges of 1.3-8.0 µg/mL and 3.3-13.3 µg/mL, respectively) and also against four other Legionella species (MIC ranges of 0.8-8.0 µg/mL and 3.3-21.3 µg/mL, respectively). Time-kill assays indicated that compounds 9 and 20 kill bacteria at a concentration equivalent to 2×MIC after 1 h and 6 h co-incubations, respectively. While oakmoss and the purified components exhibited antibacterial activity against Legionella spp., they were not active against other Gram-negative and -positive bacteria such as Escherichia coli, Pseudomonas aeruginosa, Bacillus subtilis and Staphylococcus aureus.
Oakmoss and its components are known as antibacterial agents, specifically against Legionella pneumophila. In the present study, we investigated the effects of oakmoss and its components (phenol, ...didepside and isochromen derivatives) on L. pneumophila biofilm formation, with particular reference to the bactericidal activity (minimum bactericidal concentration; MBC) of these components against the bacterial cells in the biofilm. Of the 20 compounds tested, two didepside derivatives and four phenol derivatives reduced biofilm formation by more than 50% of that observed for the control at their respective minimum inhibitory concentrations (1/2×MIC). The inhibitory activities of these compounds were either equivalent to or greater than that of the clarithromycin reference. Isochromen derivatives had no effect on biofilm formation. Analysis of bactericidal activity of didepside and isochromen derivatives revealed that three of four didepside derivatives and one of four isochromen derivatives exhibited high bactericidal activity (MBC: 32.0–74.7 µg/mL) against the L. pneumophila in the biofilm after 24 h or 48 h of co-incubation; the antibacterial activities of these compounds were almost equivalent to clarithromycin and chlorhexidine gluconate (MBC: 42.7–64.0 µg/mL) that were used as references. Thus, based on their anti-biofilm forming and bactericidal activities, didepside derivatives are considered to be good candidates for disinfectants against L. pneumophila.
Acanthamoeba castellanii, a ubiquitous organism in water environments, is pathogenic toward humans and also is a host for bacteria of the genus Legionella, a causative agent of legionellosis. ...Fragrance ingredients were investigated for their antibacterial activity against planktonic Legionella pneumophila, amoebicidal activity against A. castellanii, and inhibitory effect against L. pneumophila uptake into A. castellanii. Helional® exhibited relatively high antibacterial activity minimum inhibitory concentration (MIC) , 32.0 μg/mL . Anis aldehyde, canthoxal, helional® and vanillin exhibited amoebicidal activity (IC50 values, 58.4±2.0, 71.2±14.7, 66.8±8.3 and 49.1±2.5μg/mL, respectively) . L. pneumophila pretreatment with sub-MICs (0.25×MIC) of anis aldehyde, canthoxal, cortex aldehyde® 50 percent or vanillin evidently reduced L. pneumophila uptake into A. castellanii (p < 0.01) . Thus, fragrance ingredients were good candidates for disinfectant against L. pneumophila and A. castellanii.
Acanthamoeba castellanii, a ubiquitous organism in water environments, is pathogenic toward humans and also is a host for bacteria of the genus Legionella, a causative agent of legionellosis. ...Oakmoss, a natural fragrance ingredient, and its components are antibacterial agents specifically against the genus Legionella. In the present study, oakmoss and its components were investigated for their amoebicidal activity against A. castellanii ATCC 30234 and the inhibitory effect on the uptake of L. pneumophila JCM 7571 (ATCC 33152) into A. castellanii. The oakmoss and its components 3-hydroxy-5-methylphenyl 2,4-dihydroxy-6-methylbenzoate(5), and 6,8-dihydroxy-3-pentyl-1H-isochromen-1-one (12) exhibited high amoebicidal activity (IC50 values; 10.5 ± 2.3, 16.3 ± 4.0 and 17.5 ± 2.8 μg/mL, respectively) after 48 h of treatment, which were equivalent to that of the reference compound, chlorhexidine gluconate. Pretreatment of L. pneumophila with sub-minimal inhibitory concentration of oakmoss, compound 5, 3-hydroxy-5-methylphenyl 2-hydroxy-4-methoxy-6-methylbenzoate (10) and 8-(2,4-dihydroxy-6-pentylphenoxy)-6-hydroxy-3-pentyl-1H-isochromen-1-one (14) obviously reduced the uptake of L. pneumophila into A.castellanii (p < 0.05).The inhibitory effect of compound 5 on the uptake of L. pneumophila was almost equivalent to that of ampicillin used as a reference. Thus, the oakmoss and its components were considered to be good candidates for disinfectants against not only genus Legionella but also A. castellanii.
In the current study we investigated the antibacterial activity of fragrance ingredients against Legionella pneumophila, a causative agent of severe pneumonia. Among the 41 different fragrance ...ingredients tested, we found that the natural fragrance ingredients oakmoss (OM) and birch tar oil (BT), which contain many components, exhibit potent antibacterial activity. The minimum inhibitory concentration (MIC, % (v/v)) of OM and BT were 0.0020 and 0.0024, respectively and were lower than that of cinnamic aldehyde (0.0078), which has been previously shown to possess high antimicrobial activity. In a time–kill assay of OM and BT at MIC and two times MIC, the colony forming units (CFU) of the microbe were reduced to between 10−3 to 10−4 of the original CFU after 1 h co-incubation. After this time, the CFU gradually decreased in number, but remained above detection levels even after a 48-h co-incubation, except for BT at two times MIC. In contrast, at a concentration of 0.1% OM and BT (approximately 50 times MIC), CFU were not detected after co-incubation for 1 h. Another 18 fragrance ingredients including ketone, aldehyde, lactone, acid, phenol derivative, aliphatic alcohol and quinoline also exhibited a lesser degree of antibacterial activity against L. pneumophila at a MIC of less than 0.10.
Acanthamoeba castellanii is a ubiquitous organism found in environmental water. The amoeba is pathogenic to toward humans and is also a reservoir of bacteria of the genus Legionella, a causative ...agent of legionellosis. Oakmoss, a source of natural fragrance ingredients, and its components are antibacterial agents that are specifically active against the genus Legionella. In the present study, oakmoss and its components were investigated for their inhibitory effects on total (extra- and intracellular) Legionella pneumophila within A. castellanii and on L. pneumophila within A. castellanii. Among the oakmoss components, 3-hydroxy-5-methylphenyl 2,4-dihydroxy-6-methylbenzoate (1), 3-methoxy-5-methylphenyl 2,4-dihydroxy-6-methylbenzoate (2), and 8-(2,4-dihydroxy-6-(2-oxoheptyl)phenoxy)-6-hydroxy-3-pentyl-1H-isochromen-1-one (8) reduced the number of total bacteria (extra- and intracellular) in a test culture and also exhibited high amoebicidal activity against L. pneumophila within A. castellanii at concentrations lower than their IC50 values for A. castellanii. In contrast, 6,8-dihydroxy-3-pentyl-1H-isochromen-1-one (5) reduced the total number of L. pneumophila and, also that of total bacteria after 24 h of treatment (P < 0.05), whereas the compound did not exhibit amoebicidal activity against L. pneumophila within A. castellanii at concentrations lower than its IC50 value against A. castellanii. Thus, it is suggested that these oakmoss components could be good candidates for disinfectants to protect from Legionella infection.
We prepared carpet cleaners containing three wood oils extracted from Thujopsis dolabrata Sieb. et Zucc. var. hondai Makino, Chamaecyparis obtusa Endl., and Chamaecyparis taiwanensis Masamune et ...Suzuki and studied their effects on mites and perfumerists' impressions. The oil concentrations were set at 0.1%, 0.2%, 0.4%, 0.8%, and 1.6%. The effects on Dermatophagoides pteronyssinus Trouessart were investigated. The sensory evaluations were conducted by seven male perfumerists using the SD method and they were asked to describe freely their impressions of the scents. These results showed that: (1) all three types of wood oil had a significant effect on making D. pteronyssinus inactive at 0.1% concentration; and (2) the wood oil of T. dolabrata evoked refreshing, natural, rich, and intellectual feelings; C. obtusa oil evoked vivacious, rich, and intellectual feelings; and C. taiwanensis evoked refreshing, natural, rich, rough, masculine feelings. According to the test subjects, T. dolabrata evoked “woody” and “earthy” impressions; C. obtusa evoked “woody,” “citrus,” and “pine-resin” impressions; and C. taiwanensis evoked “woody,” “citrus,” and “medical” impressions. Many issues remain to be investigated, but the inclusion of wood oil in carpet cleaners offered both good mite control and a pleasant aroma to humans. This study suggests a new potential for using these wood oils.
Three new sesquiterpenoids were isolated from the liverwort Marsupella emarginata subsp. tubulosa. The structures and absolute configurations of the compounds have been shown to be ...(−)-marsupellone(1), (+)-marsupellol(2) and (+)-acetoxymarsupellone(3), containing an ent-longipinane skeleton, on the basis of chemical and spectral evidence.
A bent fluorenone-based dipyridyl ligand LA reacts with PdII cations to a solvent-dependent dynamic library of Pd n L2n assemblies, constituted by a Pd3LA 6 ring and a Pd4LA 8 tetrahedron as major ...components, and a Pd6LA 12 octahedron as minor component. Introduction of backbone steric hindrance in ligand LB allows exclusive formation of the Pd6LB 12 octahedron. Combining equimolar amounts of both ligands results in integrative self-sorting to give an unprecedented Pd4LA 4LB 4 heteroleptic tetrahedron. Key to the non-statistical assembly outcome is exploiting the structural peculiarity of the Pd4L8 tetrahedral topology, where the four lean ligands occupy two doubly bridged edges and the bulky ligands span the four remaining, singly bridged edges. Hence, the system finds a compromise between the entropic drive to form an assembly smaller than the octahedron and the enthalpic prohibition of pairing two bulky ligands on the same edge of the triangular ring. The emission of luminescent LA is maintained in both homoleptic Pd3LA 6 and heteroleptic Pd4LA 4LB 4.
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