Commercially available essential oils extracted from Artemisia dracunculus L., Inula graveolens L., Lavandula officinalis Chaix, and Ocimum sanctum L. and the components of these oils were screened by the microplate assay method for determining their acetylcholinesterase (AChE) inhibitory activity. The composition profiles of the oils were characterized by gas chromatography-mass spectrometry (GC-MS) analysis, and the relationships between the oil components and the AChE inhibitory activity of the oils were outlined. The results showed that all of the oils, except that of A. dracunculus from Hungary, exhibited AChE inhibitory activity, and the A. dracunculus oil from France showed the most potent inhibitory activity [50% inhibition concentration (IC(50)) = 0.058 mg/mL]. The AChE inhibitory activity of I. graveolens oil has not been reported to date, and this study is the first to reveal this activity in the oil. Among the essential oil components, five components, namely, 1,8-cineole, α-pinene, eugenol, α-terpineol, and terpinen-4-ol, showed AChE inhibitory activity, with IC(50) values of 0.015, 0.022, 0.48, 1.3, and 3.2 mg/mL, respectively. Eugenol, in particular, was found to be a potent AChE inhibitor along with determination of the IC(50) value, a finding that has been reported for the first time in this study. However, the ratio of the contribution of the active components, including a novel AChE inhibitor, to the observed AChE inhibitory activity of the essential oils was not very high. The results of this study raise concerns about the AChE inhibitory activity of widely produced and readily accessible commercial essential oils.
Chlorinated polycyclic aromatic hydrocarbons (ClPAHs) with 3-5 rings are ubiquitous environmental contaminants. However, toxicities of ClPAHs remain unclear. In this study, aryl hydrocarbon receptor (AhR)-mediated activities of ClPAHs were investigated by using a yeast assay system. All environmentally relevant 18 ClPAHs showed the AhR activities in the test; the activities were elevated with the number of chlorine atoms on the lower molecular weight PAH ( approximately three-ring and fluoranthene derivatives) but not for higher molecular weight ClPAHs (>four-ring). The similar trends were also observed in certain ClPAHs-induced cytochrome P450 1A1 expression in MCF-7 cells. The structure-activity relationship between the AhR activity and the corresponding solvent accessible surface area of ClPAHs revealed a parabolic relationship, with approximately 350 A (2)/molecule as the optimal dimensions as the ligand for binding to AhR. These findings indicate that the spatial dimensions of ClPAHs apparently influence their ability to activate the AhR. Finally, we discussed the toxicity of exposure to ClPAHs based on the AhR activities, estimated that it would be approximately 30-50 times higher than that of dioxins.
Superaromatic stabilization energy (SSE), previously proposed by us, can be used as a novel local aromaticity index for benzene rings in polycyclic aromatic hydrocarbons (PAHs). SSE can be interpreted as the first local aromaticity index explicitly related to all relevant circuits in a polycyclic π-system, an origin of local aromaticity, being free of local aromaticity arising from adjacent six-site circuits. Therefore, this quantity is best suited for characterizing the electronic structure of large pericondensed PAHs and graphene nanoflakes.
Recently synthesized septulene is a unique cycloarene molecule in that no macrocyclic conjugation circuits can be chosen from the π-system. This molecule has essentially no superaromatic stabilization energy (SSE) and can be viewed as an ideal nonsuperaromatic macrocycle. SSEs for kekulene and other cycloarenes are also very small. In these hydrocarbons, a macrocycle formed by fused benzene rings effectively suppresses not only the aromaticity inherent in macrocyclic (4n+2)-site conjugation circuits but also the antiaromaticity inherent in macrocyclic (4n±1)-site circuits. Comparative study of superaromaticity in multilayered coronoid hydrocarbons revealed that not only SSE but also the HOMO contribution to SSE is minimized in odd-layered coronoids.
The atmospheric levels of 12 chlorinated polycyclic aromatic hydrocarbons (ClPAHs) associated with particulates at an urban site in Japan were investigated. Only 7 of the 12 species studied were detected in air samples collected monthly during 2002. 1-Chloropyrene (1-ClPy) was detected at the highest concentration (7.5 pg m -3 (annual mean)), followed by 6-chlorobenzo[a]pyrene (6-ClBaP; 5.6 pg m -3 ) and 9,10-dichlorophenanthrene (5.1 pg m -3 ). The concentrations of the ClPAHs tended to be higher in winter than in summer, with the exception of the 6-ClBaP concentration, which was high in both summer and winter. Correlation analysis also indicated that the behavior of 6-ClBaP differed significantly from that of the other ClPAHs. Comparison of the atmospheric ClPAH concentration profile normalized to 1-ClPy concentration with that for a traffic air sample revealed significant differences between the profiles. The behavior of the atmospheric ClPAHs was also influenced by the origin of the associated particulates, which varied according to season. The positions of chlorination in the detected ClPAHs were consistent with those where the frontier electron density was high. This means that the atmospheric ClPAHs were formed by secondary reactions with chlorine atoms. The photostabilities of the ClPAHs were also investigated in laboratory experiments using a chemical model system. The ClPAHs decayed according to first-order reaction rate kinetics, with photostabilities increasing in the order 6-ClBaP < 1-ClPy < 7-ClBaA < ClPhe < ClFluor, consistent with the trend for the parent PAHs. The photolyses of chlorophenanthrenes and 7-chlorobenz[a]anthracene were confirmed to proceed by initial abstraction of chlorine, followed by oxidative degradation. ES040433SFIGURE 4. Chemical structures of the ClPhe derivatives and 7-ClBaA used in the irradiation experiments.
According to the bridged annulene model, macrocyclic aromaticity of a porphyrinoid species can be attributed to the annulene-like main macrocyclic conjugation pathway (MMCP). Macrocyclic aromaticity, however, is given theoretically as a sum of contributions from all macrocyclic circuits. We found that the aromaticity due to each macrocyclic circuit is determined formally but broadly by Hückel's [4n + 2] rule of aromaticity. Nitrogen atoms in the pyrrolic rings effectively suppress the variation in the number of π electrons staying along each macrocyclic circuit. As a result, all or most macrocyclic circuits in oligopyrrolic macrocycles are made aromatic (or antiaromaitc) in phase with the MMCP. Thus, the MMCP is not a determinant of macrocyclic aromaticity but can be regarded as a good indicator of this quantity. This is why the bridged annulene model appears to hold for many porphyrins.
The acute toxicity of 21 parabens and their chlorinated derivatives was investigated by means of two toxicity bioassays: Daphnia magna immobilization test and the inhibition of bioluminescence of Vibrio fischeri. The median effective concentration (EC(50)) values of the tested parabens ranged from 2.2 to 62 mg l(-1) in the D. magna test and from 0.0038 to 5.9 mg l(-1) in the V. fischeri test at 15 min after exposure. The toxicity of dichlorinated methyl- and n-propylparaben, the most commonly used preservatives in cosmetics, toward D. magna was 3.9- and 2.8-fold that of their corresponding parent compounds. Toxicity toward D. magna showed a linear relationship with log P, indicating that toxicity increases with increasing hydrophobicity. On the other hand, the correlations of toxicity toward V. fischeri with hydrophobicity and with the degree of chlorination were poor. In addition, the results of the present study indicated that the V. fischeri test was more sensitive than the D. magna test for the determination of the acute toxicity of parabens. A complete assessment of the ecological and toxicological risks of parabens may require the examination of chlorinated parabens as well as the parent pollutants, as described in the present study.
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