a b s t r a c tThis study evaluated the cytotoxicity activity of the essential oils of Tagetes erecta L., Asteraceae (TE-OE), Tetradenia riparia (Hochst.) Codd, Lamiaceae (TR-OE), Bidens sulphurea (Cav.) Sch. Bip., Asteraceae (BS-OE), and Foeniculum vulgare Mill., Apiaceae (FV-OE), traditionally used in folk medicine, against the tumor cell lines murine melanoma (B16F10), human colon carcinoma (HT29), human breast adenocarcinoma (MCF-7), human cervical adenocarcinoma (HeLa), human hepatocellular liver carcinoma (HepG2), and human glioblastoma (MO59J, U343, and U251). Normal hamster lung fibroblasts (V79 cells) were included as control. The cells were treated with essential oil concentrations ranging from 3.12 to 400 g/ml for 24 h. The cytotoxic activity was evaluated using the XTT assay; results were expressed as IC 50 , and the selectivity index was calculated. The results were compared with those achieved for classic chemotherapeutic agents. TE-OE was the most promising among the evaluated oils: it afforded the lowest IC 50 values for B16F10 cells (7.47 ± 1.08 g/ml) and HT29 cells (6.93 ± 0.77 g/ml), as well as selectivity indices of 2.61 and 2.81, respectively. The major BS-EO, FV-EO and TE-EO chemical constituents were identified by gas chromatography mass spectrometry as being (E)-caryophyllene (10.5%), germacrene D (35.0%) and 2,6-di-tert-butyl-4-methylphenol (43.0%) (BS-EO); limonene (21.3%) and (E)-anethole (70.2%) (FV-EO); limonene (10.4%), dihydrotagetone (11.8%), ␣-terpinolene (18.1%) and (E)-ocimenone (13.0%) (TE-EO); and fenchone (6.1%), dronabinol (11.0%), aromadendrene oxide (14.7%) and (E,E)-farnesol (15.0%) (TR-EO). 2,6-di-tert-butyl-4-methylphenol (43.0%), (E)-anethole (70.2%) and ␣-terpinolene (18.1%), respectively. These results suggest that TE-OE may be used to treat cancer without affecting normal cells.
This work used the broth microdilution method to investigate the antimicrobial activity of the essential oil obtained from the leaves of Plectranthus neochilus (PN-EO) against a representative panel of oral pathogens. We assessed the antimicrobial activity of this oil in terms of the minimum inhibitory concentration (MIC). PN-EO displayed moderate activity against Enterococcus faecalis (MIC = 250 μg/mL) and Streptococcus salivarus (MIC = 250 μg/mL), significant activity against Streptococcus sobrinus (MIC = 62.5 μg/mL), Streptococcus sanguinis (MIC = 62.5 μg/mL), Streptococcus mitis (MIC = 31.25 μg/mL), and Lactobacillus casei (MIC = 31.25 μg/mL), and interesting activity against Streptococcus mutans (MIC = 3.9 μg/mL). GC-FID and GC-MS helped to identify thirty-one compounds in PN-EO; α-pinene (1, 14.1%), β-pinene (2, 7.1%), trans-caryophyllene (3, 29.8%), and caryophyllene oxide (4, 12.8%) were the major chemical constituents of this essential oil. When tested alone, compounds 1, 2, 3, and 4 were inactive (MIC > 4000 μg/mL) against all the microorganisms. These results suggested that the essential oil extracted from the leaves of Plectranthus neochilus displays promising activity against most of the evaluated cariogenic bacteria, especially S. mutans.
Abstract:The in vitro schistosomicidal effects of the essential oil obtained from Tagetes erecta L. Asteraceae, leaves (TE-EO) collected in Brazil against Schistosoma mansoni worms are reported in this paper. The oil caused a significant decrease in the motor activity at 50 μg/mL as minimal concentration after 24 h. This oil also caused death of all the parasites and the separation of coupled pairs into individual male and female at 100 μg/mL after 24 h. The viability of adult worm groups treated with the TE-EO at 100 μg/mL was similar to that of groups treated with praziquantel (positive control). In addition, the oil promoted the inhibition of eggs development at all the tested concentrations. These data indicate that the TE-EO could be considered as a promising source for the development of new schistosomicidal agents.
Dental prosthesis supports Candida species growth and may predispose the oral cavity to lesions. C. tropicalis has emerged as a colonizer of prosthesis and has shown resistance to clinically used antifungal agents, which has increased the search for new antifungals. This work describes the effectiveness of fifteen essential oils (EOs) against C. tropicalis The EOs were obtained by hydrodistillation and were chemically characterized by gas chromatography-mass spectrometry. The antifungal activities of the EOs were evaluated by the microdilution method and showed that Pelargonium graveolens (Geraniaceae) (PG-EO) was the most effective oil. Geraniol and linalool were the major constituents of PG-EO. The 2,3-Bis-(2-Methoxy-4-Nitro-5-Sulfophenyl)-2H-Tetrazolium-5-Carboxanilide (XTT) assay showed that all the clinical C. tropicalis strains formed viable biofilms. Scanning electron microscopy examination of the biofilms revealed a complex architecture with basal layer of yeast cells and an upper layer of filamentous cells. Treatments with PG-EO, linalool, and geraniol significantly reduced the number of viable biofilm cells and inhibited biofilm formation after exposure for 48 h. PG-EO, geraniol, and linalool were not toxic to normal human lung fibroblasts (GM07492A) at the concentrations they were active against C. tropicalis Together, our results indicated that C. tropicalis is susceptible to treatment with PG-EO, geraniol, and linalool, which could become options to prevent or treat this infection.
We have investigated the chemical composition and the antibacterial activity of the essential oil of Dysphania ambrosioides (L.) Mosyakin & Clemants (Chenopodiaceae) (DA-EO) against a representative panel of cariogenic bacteria. We have also assessed the in vitro schistosomicidal effects of DA-EO on Schistosoma mansoni and its cytotoxicity to GM07492-A cells in vitro. Gas chromatography (GC) and gas chromatography-mass spectrometry (GC/MS) revealed that the monoterpenes cis-piperitone oxide (35.2%), p-cymene (14.5%), isoascaridole (14.1%), and α-terpinene (11.6%) were identified by as the major constituents of DA-EO. DA-EO displayed weak activity against Streptococcus sobrinus and Enterococcus faecalis (minimum inhibitory concentration (MIC) = 1000 μg/ml). On the other hand, DA-EO at 25 and 12.5 μg/ml presented remarkable schistosomicidal action in vitro and killed 100% of adult worm pairs within 24 and 72 h, respectively. The LC values of DA-EO were 6.50 ± 0.38, 3.66 ± 1.06, and 3.65 ± 0.76 μg/ml at 24, 48, and 72 h, respectively. However, DA-EO at concentrations higher than 312.5 μg/ml significantly reduced the viability of GM07492-A cells (IC = 207.1 ± 4.4 μg/ml). The selectivity index showed that DA-EO was 31.8 times more toxic to the adult S. mansoni worms than GM07492-A cells. Taken together, these results demonstrate the promising schistosomicidal potential of the essential oil of Dysphania ambrosioides.
We investigated the gas-phase fragmentation reactions of a series of 2-aroylbenzofuran derivatives by electrospray ionization tandem mass spectrometry (ESI-MS/MS). The most intense fragment ions were the acylium ions m/z 105 and [M+H-C H ] , which originated directly from the precursor ion as a result of 2 competitive hydrogen rearrangements. Eliminations of CO and CO from [M+H-C H ] were also common fragmentation processes to all the analyzed compounds. In addition, eliminations of the radicals •Br and •Cl were diagnostic for halogen atoms at aromatic ring A, whereas eliminations of •CH and CH O were useful to identify the methoxyl group attached to this same ring. We used thermochemical data, obtained at the B3LYP/6-31+G(d) level of theory, to rationalize the fragmentation pathways and to elucidate the formation of E, which involved simultaneous elimination of 2 CO molecules from B.
We have investigated gas‐phase fragmentation reactions of protonated benzofuran neolignans (BNs) and dihydrobenzofuran neolignans (DBNs) by accurate‐mass electrospray ionization tandem and multiple‐stage (MSn) mass spectrometry combined with thermochemical data estimated by Computational Chemistry. Most of the protonated compounds fragment into product ions B ([M + H–MeOH]+), C ([B–MeOH]+), D ([C–CO]+), and E ([D–CO]+) upon collision‐induced dissociation (CID). However, we identified a series of diagnostic ions and associated them with specific structural features. In the case of compounds displaying an acetoxy group at C‐4, product ion C produces diagnostic ions K ([C–C2H2O]+), L ([K–CO]+), and P ([L–CO]+). Formation of product ions H ([D–H2O]+) and M ([H–CO]+) is associated with the hydroxyl group at C‐3 and C‐3′, whereas product ions N ([D–MeOH]+) and O ([N–MeOH]+) indicate a methoxyl group at the same positions. Finally, product ions F ([A–C2H2O]+), Q ([A–C3H6O2]+), I ([A–C6H6O]+), and J ([I–MeOH]+) for DBNs and product ion G ([B–C2H2O]+) for BNs diagnose a saturated bond between C‐7′ and C‐8′. We used these structure‐fragmentation relationships in combination with deuterium exchange experiments, MSn data, and Computational Chemistry to elucidate the gas‐phase fragmentation pathways of these compounds. These results could help to elucidate DBN and BN metabolites in in vivo and in vitro studies on the basis of electrospray ionization ESI‐CID‐MS/MS data only.
The antibacterial activity of nine selected essential oils (EOs) against a panel of oral pathogens was investigated in terms of their minimum inhibitory concentrations (MICs) by using the broth microdilution method. Most of the EOs displayed weak activity or were inactive against the selected oral pathogens, with MIC values ranging from 500 to 4000 μg/mL. However, the EO obtained from the leaves of Bidens sulphurea (Asteraceae) was found to display moderate activity against Streptococcus mutans (MIC = 250 μg/mL) and significant activity against Streptococcus mitis (MIC = 31.25 μg/mL). Germacrene D (38.3%), trans-caryophyllene (18.0%), β-elemene (13.9%) and bicyclogermacrene (13.1%) were identified as the main chemical components of this oil. 2,6-Di-tert-butyl-4-methylphenol, previously described as the major constituent in the EO from the flowers of B. sulphurea, was not detected in this study.
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