Insecticidal properties of essential oils against Tribolium castaneum (Herbst) and their inhibitory effects on acetylcholinesterase and adenosine triphosphatases

Essential oils from 20 Egyptian plants were obtained by using hydrodistillation. The chemical composition of the isolated oils was identified by gas chromatograph/mass spectrometer. Fumigant and contact toxicities of the essential oils were evaluated against the adults of Tribolium castaneum. In fumigation assays, the oil of Origanum vulgare (LC₅₀ = 9.97 mg/L air) displayed the highest toxicity towards the adults of T. castaneum. In contact assays, the oils of Artemisia monosperma (LC₅₀ = 0.07 mg/cm²) and O. vulgare (LC₅₀ = 0.07 mg/cm²) were the most potent toxicants against the adults of T. castaneum. Biochemical studies showed that the tested oils caused pronounced inhibition of acetylcholinesterase (AChE) and adenosine triphosphatases (ATPases) isolated from the larvae of T. castaneum. The oil Cupressus macrocarpa (IC₅₀ = 12.3 mg/L) was the most potent inhibitor of AChE, while the oil of Calistemon viminals (IC₅₀ = 4.4 mg/L) was the most potent inhibitor of ATPases.     

Chemical composition,antioxidant and antiproliferative activities of essential oil from rhizome and leaves of Curcuma mutabilis Škorničk., M. Sabu & Prasanthk., endemic to Western Ghats of India

Abstract

Hydro-distilled essential oils, from fresh rhizomes and leaves of Curcuma mutabilis ?korni?k., M.Sabu & Prasanthk., characterized by GC–MS revealed the presence of thirty three and twenty three compounds therein respectively. Whilst estrone methyl ether (3-Methoxyestra-1,3,5(10)-trien-17-one) was the major component in rhizome oil (47.35%), sesquiterpene hydrocarbons predominated as the major group (63.92%) in leaf oil with a higher preponderance of β-caryophyllene (25.48%), β-farnesene (19.47%) and α-humulene (11.01%). Weak antioxidant activities observed in these oils determined by DPPH and ABTS methods were apparently influenced both by the oil composition and the assay conditions. Rhizome oil showed higher antiproliferative activity than leaf oil against leukemic K562 (IC₅₀-6.8µg/mL) and colorectal HCT116 (IC₅₀-8.5µg/mL) cancer cell lines. This first report reveals composition and biological activities of essential oils from C. mutabilis.     

Neoclerodane diterpenoids from Scutellaria barbata with cytotoxic activities

Abstract

Two new neoclerodane diterpenoids, barbatin F (1), barbatin G (2) together with four known compounds, scutebata A (3), scutebata B (4), scutebata C (5) and scutebata P (6) were isolated from the whole plant of Scutellaria barbata D.Don. Their structures were elucidated on the basis of spectroscopic studies. In vitro cytotoxicity of selected compounds against cancer cell lines LoVo, SMMC-7721, HCT-116, and MCF-7 were evaluated, compound 1 and 2 showed weak cytotoxic activities against HCT-116 colon cancer cell lines with IC₅₀ value of 44.3, 32.3?μM, respectively, while compound 3 and 4 exhibited moderate cytotoxic activities against four tested human cancer cell lines with IC₅₀ values of 5.31～28.5?μM.     

Perisomalien A,a new cytotoxic scalarane sesterterpene from the fruits of Periploca somaliensis

Abstract

The CHCl₃ fraction of MeOH extract of Periploca somaliensis (family Asclepiadaceae) fruits afforded a new scalarane sesterterpene, namely perisomalien A (1), along with lupeol acetate (2), β-amyrin (3), cycloart-23Z-ene-3β,25-diol (4), and β-sitosterol-3-O-β-D-glucopyranoside (5). Their chemical structures were established by various spectroscopic analyses, in addition to comparison with the formerly reported data. Moreover, the cytotoxic activity of these metabolites was assessed towards MCF-7, HepG2, and HCT-116 tumour cell lines using sulforhodamine B (SRB) assay. Compound 4 showed the most potent cytotoxic profile with IC₅₀ 9.0?µM towards MCF-7, compared to doxorubicin (IC₅₀ 0.18?µM). Also, 1 and 4 possessed the most potent effect towards HepG2 with IC₅₀s 26.7 and 25.9?μM, respectively. In addition, all tested compounds showed cytotoxic effects with IC₅₀ values ranging from 19.9 to 39.3?µM against HCT-116.     

Chemical composition and biological evaluation of the volatile constituents from the aerial parts of Nephrolepis exaltata (L.) and Nephrolepis cordifolia (L.) C. Presl grown in Egypt

The essential oil from the aerial parts of Nephrolepis exaltata and Nephrolepis cordifolia obtained by hydro-distillation were analyzed by gas chromatography/ mass spectrometry. The essential oils exhibited potential antibacterial and antifungal activities against a majority of the selected microorganisms. NEA oil showed promising cytotoxicity in breast, colon and lung carcinoma cells. The results presented indicate that NEA oil could be useful alternative for the treatment of dermatophytosis.

Comparative investigation of hydro-distilled volatile constituents from aerial parts (A) of Nephrolepis exaltata (NE) and Nephrolepis cordifolia (NC) (Family Nephrolepidaceae) was carried out. Gas chromatography/mass spectrometry revealed that oils differ in composition and percentages of components. Oxygenated compounds were dominant in NEA and NCA. 2,4-Hexadien-1-ol (16.1%), nonanal (14.4%), β-Ionone (6.7%) and thymol (2.7%) were predominant in NEA. β-Ionone (8.0%), eugenol (7.2%) and anethol (4.6%) were the main constituents in NCA. Volatile samples were screened for their antibacterial and antifungal activities using agar diffusion method and minimum inhibitory concentrations. The cytotoxic activity was evaluated using viability assay in breast (MCF-7), colon (HCT-116) and lung carcinoma (A-549) cells by the MTT assay. The results revealed that NEA oil exhibited potential antimicrobial activity against most of the tested organisms and showed promising cytotoxicity.     

Effect of bioclimatic area on the composition and bioactivity of Tunisian Rosmarinus officinalis essential oils

The chemical composition of eight Tunisian Rosmarinus officinalis L. populations (A–H) from different bioclimatic areas has been examined by gas chromatography (GC) and GC-mass spectrometry. The essential oils are characterised by high amounts of oxygenated monoterpenes (58.2–71.7%) followed by monoterpene hydrocabons (15.1–26.7%). 1,8-Cineole, camphor, α-pinene and borneol are the main representative components. The antioxidant activity was investigated by 2,2-diphenyl-1-picrylhydrazyl radical (DPPH), ferric reducing ability power assay and β-carotene bleaching test. Samples showed antiradical activity by inhibiting DPPH radical with IC₅₀ values ranging from 375.3 to 592.8 μg mL^? 1 for samples F and A, respectively. Sample A also showed the most promising activity in β-carotene bleaching test (IC₅₀ of 31.9 μg mL^? 1). The essential oils were also screened for acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity. Sample G showed the highest activity against AChE (IC₅₀ of 64.7 μg mL^? 1) while sample D (IC₅₀ of 29.5 μg mL^? 1) exhibited the most potent activity against BChE.     

Evaluation of chemical composition,antioxidant and anti-hyperglycemic activities of the essential oil based nanoemulsions of Cinnamomum litseifolium

In the present study, antioxidant and anti-hyperglycemic activities of nanoemulsions of the leaf essential oils of Cinnamomum litseifolium Thwaites collected from two different locations in the Western Ghats namely, Kannikatty, Kalakad Mundandurai Tiger Reserve, Tamil Nadu (Cl¹) and Karamanayar, Agasthyamalai hills, Kerala (Cl²), India were studied. Essential oils were extracted from the leaves and characterized by GC-FID and GC-MS. Slight variation in the composition of leaf essential oils was observed. Essential oil based nanoemulsions were prepared using a surfactant (Tween-80), co-surfactant (propylene glycol) and an emulsifier (lecithin) by homogenization followed by ultra-sonication. Upon characterization, the nanoemulsion of Cl¹ showed better stability than Cl². Both nanoemulsions inhibited α-amylase and α-glucosidase enzymes with IC₅₀ values of 1.998 and 0.780 mg/mL for Cl¹ and 3.587 and 1.455 mg/mL for Cl² respectively.     

Cytotoxic constituents from Vicia monantha subsp. monantha seeds

Chemical investigation of Vicia monantha subsp. monantha Retz. revealed isolation of one new hydroxy- fatty acid (6) identified as (6-Z, 10-E)-9-hydroxy henicosa-6,10-dienoic acid in addition to six known metabolites; hexadecanoic acid (1), β-sitosterol (2), β-amyrin (3), β-sitosterol-glucoside (4), 2,3-dihydroxypropyl tetradecanoate (5) and (Z)-9-hydroxypentadec-6-enoic acid (7). The cytotoxic effect of the isolated compounds was assessed by MTT assay using lung cancer A-549, prostate cancer PC3, breast cancer MCF-7, colon cancer HCT-116 and liver cancer HepG2 cell lines. Only compounds 1, 2, and 4 showed cytotoxic effect on HCT-116 cells where compound 2 was the most active with IC₅₀ value of 22.61 μg/mL. In addition, compounds 1, 2, 3, and 4 showed promising cytotoxic effect on MCF-7 cells with IC₅₀ values of 21.03, 15.42, 10.089, and 11.34 μg/mL, respectively.     

Synthesis and in vitro cytotoxicity of platinum(II) complexes with chiral N-monosubstituted 1,2-cyclohexyldiamine derivatives as the carrier groups

Eight platinum(II) complexes with the new chiral ligands, (1R,2R)-N ¹-(pyridine-2-ylmethyl) cyclohexane-1,2-diamine (R) or (1S,2S)-N ¹-(pyridine-2-ylmethyl) cyclohexane-1,2-diamine (S) as the carrier groups were designed, synthesized, and spectrally characterized. All platinum(II) complexes showed much better aqueous solubility than cisplatin and oxaliplatin. In vitro cytotoxicity of the compounds against human HepG-2, MCF-7, A549, and HCT-116 cell lines was evaluated. Results indicate that all compounds with R as the carrier group showed cytotoxicity against HCT-116, A549, and MCF-7 cell lines; however, all compounds with S as carrier group exhibited disappointing cytotoxicity against tested cell lines. Compound R2, bearing ClCH₂COO^- as leaving group, exhibited better cytotoxicity than that of carboplatin against A549 and MCF-7 cell lines and also showed close activity to oxaliplatin against HCT-116 cell line.     

Identification of antibacterial and antioxidant constituents of the essential oils of Cynanchum chinense and Ligustrum compactum

The aim of this research was to determine the chemical composition, antioxidant and antibacterial properties of the essential oils from Cynanchum chinense and Ligustrum compactum and isolation of antioxidant and antibacterial constituents from the essential oils. Thirty-eight components were identified in essential oils. Based on bioactivity-guided fractionation, guaiacol, linalool and 2-phenylethanol were isolated and identified as active constituents. Both L. compactum flower oil and 2-phenylethanol showed high antibacterial performance, with inhibition zone from 22.8 ± 0.8 to 11.9 ± 2.0 mm at highest concentration, and minimum inhibitory concentration values ranging from 0.25% to 1%. In both DPPH and ABTS assay, the active constituent guaiacol (IC₅₀ = 4.15 ± 0.72 and 9.12 ± 0.98 μg mL^? 1, respectively) exhibited high antioxidant activity, and the oils showed moderate antioxidant activity. These results indicate potential efficacy of active constituents and essential oils of L. compactum and C. chinense to control food-borne pathogenic and spoilage bacteria.     

Chemical composition of the Brazilian native Cinnamomum stenophyllum (Meisn.) Vattimo-Gil essential oil by GC-qMS and GC × GC-TOFMS,and its cytotoxic activity

Cinnamomum stenophyllum (Meisn.) Vattimo-Gil (Lauraceae) is a native and vulnerable Brazilian species restricted to the Atlantic Forest. The leaf essential oil obtained by hydrodistillation was characterized for the first time by two-dimensional gas chromatography with time-of-flight mass spectrometry (GC × GC-TOFMS). This analysis resulted in the tentatively identification of 80 compounds, showing the superior performance of this method in comparison to the seven compounds identified by GC–MS. The identified compounds included 8 ketones, 7 monoterpene hydrocarbons, 30 oxygenated monoterpenes, 4 sesquiterpene hydrocarbons and 23 oxygenated sesquiterpenes, showing that the C. stenophyllum oil contained mostly oxygenated mono and sesquiterpenes. The oil cytotoxicity was tested against two human cancer cell lines, colon adenocarcinoma (HCT-116) and breast cancer carcinoma (MCF-7), and the non-tumor retinal pigment epithelial cells (RPE) using the colorimetric MTT assay. Both cancer cell lines were sensible to leaf essential oil, with IC₅₀ < 20 μg/mL (HCT, IC₅₀ = 9.95 μg/mL and MCF-7, IC₅₀ = 16.65 μg/mL), while there was no cytotoxicity against the non-tumor cells at tested concentrations (IC₅₀ > 50 μg/mL), suggesting selectivity to cancer cells. The results showed that the C. stenophyllum leaf essential oil has a cytotoxic potential, presenting several compounds already known as biologically active against tumor cells.     

TLC–direct bioautography as a method for evaluation of antibacterial properties of Thymus vulgaris L. and Salvia officinalis L. essential oils of different origin

ABSTRACT

The dot-blot bioautography was used to evaluate the antibacterial properties of Thymus vulgaris L. and Salvia officinalis L. essential oils (EOs) produced by three different manufacturers. The whole samples were applied at three concentrations on thin-layer chromatography (TLC) plates which were then subjected to bioautography against Bacillus subtilis. The samples of the highest activity were found. Then, they were separated using TLC and once again subjected to bioautography against B. subtilis. As was proved, only the essential oils of T. vulgaris L. possessed strong antibacterial properties for which mostly thymol and carvacrol were responsible. Their contents were calculated using TLC–UV densitometry. The highest contents were found in the essential oils of the highest antibacterial activity revealed in the dot-blot test. It means that a dot-blot test can be used for simple and fast evaluation of antibacterial properties of essential oils.     

Analysis of essential oils from Voacanga africana seeds at different hydrodistillation extraction stages: chemical composition,antioxidant activity and antimicrobial activity

In this study, essential oils from Voacanga africana seeds at different extraction stages were investigated. In the chemical composition analysis, 27 compounds representing 86.69–95.03% of the total essential oils were identified and quantified. The main constituents in essential oils were terpenoids, alcohols and fatty acids accounting for 15.03–24.36%, 21.57–34.43% and 33.06–57.37%, respectively. Moreover, the analysis also revealed that essential oils from different extraction stages possessed different chemical compositions. In the antioxidant evaluation, all analysed oils showed similar antioxidant behaviours, and the concentrations of essential oils providing 50% inhibition of DPPH-scavenging activity (IC₅₀) were about 25 mg/mL. In the antimicrobial experiments, essential oils from different extraction stages exhibited different antimicrobial activities. The antimicrobial activity of oils was affected by extraction stages. By controlling extraction stages, it is promising to obtain essential oils with desired antimicrobial activities.     

Chemical composition,antimicrobial and antioxidant activities of the essential oils of three Uzbek Lamiaceae species

The chemical composition of the essential oil from the aerial parts of three Lamiaceae species from Uzbekistan was investigated by GC-MS analysis. β-Linalool (26.6%), α-terpineol (10.0%), coumarin (8.9%) and 4,5,7,7α-tetrahydro-4,4,7α-trimethyl-2(6H)-benzofuranone (5.4%) resulted as the main components of Ajuga turkestanica essential oil, while camphene (17.1%), 1,8-cineole (15.9%), β-cymene (7.9%) and limonene (7.4%) in Phlomis regelii. The essential oil of Thymus seravschanicus was dominated by thymol (37.5%), phellandral (26.0%), τ-terpinene (6.6%) and β-cymene (5.2%). The essential oils had considerable antimicrobial activity against different bacterial strains and fungi. Among the tested samples of essential oils, P. regelii essential oil has the significant antioxidant activity with IC₅₀ value of 117.8 ± 8.02 μg/mL.     

Chemical composition and biological activities of the essential oil from Pulicaria undulata (L.) C. A. Mey. growing wild in Egypt

Abstract

Pulicaria undulata is used as a traditional herbal remedy in Egypt. We used gas chromatography-mass spectrometry for analysis of essential oil of this plant growing wild in Egypt and 64 compounds were identified. The oil was rich in oxygenated monoterpenes (64.0%) and aromatic derivatives (18.8%). The major components were carvacrol (46.5%), xanthoxylin (18.1%) and carvotanacetone (8.7%). The oil of the Egyptian plant showed significant differences from the oil results reported on this species derived from different accessions. Antioxidant activity was performed by FRAP, DPPH and ABTS assays, and the oil demonstrated a powerful antioxidant properties. Furthermore, cytotoxicity was assessed using MTT assay against three cell lines (A375, T98G, HCT116) and the oil showed moderate results with IC₅₀ of 18.53, 40.64 and 22.23?μg/ml; respectively. The oil showed a good anti-acetylcholinesterase activity (IC₅₀?=?139.2?μg/ml) using Ellman method. In conclusion, the studied oil exhibited a peculiar fingerprint and promising biological activities.     

Synthesis,cytotoxicity, and interaction with DNA of platinum(II) complexes of (1R,2R)-N1-2-amyl-1,2-diaminocyclohexane

(1R,2R)-N¹-2-amyl-1,2-diaminocyclohexane, which has an amyl substituent as compared with 1,2-diaminocyclohexane, was used as the carrier group to construct three platinum(II) complexes. MTT assay revealed that the complexes showed decent cytotoxicity against all of the four tested tumor cell lines with the IC₅₀ values ranging from 1.08 to 253.36 μM. Particularly, the IC₅₀ values of 2 against A549 and HCT-116 reached 3.32 and 1.08 μM, respectively, which were much lower than those of cisplatin and oxaliplatin. Flow cytometry demonstrated that 2 inhibited HepG2 cells proliferation and caused cytotoxicity by inducing apoptosis and arresting cells in the G2 phase. Furthermore, agarose gel electrophoresis showed that 2 had the ability to interact with DNA in a manner different from cisplatin and oxaliplatin, indicating the carrier ligand with an alkyl moiety had an influence on the action mode of the complex.     

Chemical composition and biological activities of essential oil from Filifolium sibiricum (L.) Kitam

The essential oil from Filifolium sibiricum (L.) Kitam were extracted using hydrodistillation and GC-MS was used to analyse the essential oil. The main components were espatulenol (8.55%), geranyl acetate (8.03%), caryophyllene oxide (5.47%), calamenene (4.79%), geraniol (4.28%), calamenene (4.53%), geraniol (4.06%), cedrene epoxide (3.23%), myrtenol (3.18%), transgeranylgeranio (3.13%), etc. The essential oil showed intensive inhibitory effects against MCF-7 with IC₅₀ level of 0.78 mg/mL, HepG-2 with IC₅₀ level of 0.44 mg/mL, SKOV-3 with IC₅₀ level of 0.27 mg/mL, BGC-823 with IC₅₀ level of 0.34 mg/mL. In the antibacterial test, the essential oil showed the significant antibacterial activities. The MIC and MBC values were 5.20 and 5.20 mg/mL against Staphylococcus aureus.     

Study of the structure,prooxidative, and cytotoxic activity of some chelate copper(II) complexes

The six chelate N,O-copper(II) complexes were synthesised starting from salicylaldehyde anil Schiff bases, as ligands. Their structure is elucidated using experimental and theoretical tools. In vitro biological activities, i.e. cytotoxic and prooxidative effects against human epithelial mammary gland/breast metastatic carcinoma MDA-MB-231, epithelial colorectal carcinoma HCT-116, and foetal lung fibroblast healthy MRC-5 cell lines of investigated compounds are also determined. Complexes Cu-1, Cu-6, and especially Cu-7 showed significant cytotoxic effects, with IC₅₀ values comparable with effects of positive control CisPt. In addition, investigated complexes induced extreme oxidative and nitrosative stress in all treated cell lines. The most prominent effect is observed on HCT-116 cells, and on MRC-5 cells, while MDA-MB-231 cells showed higher resistance to the investigated cell lines, giving us direction towards the substances with more specific selectivity.     

Chemical variability and antioxidant activity of Cedrus atlantica Manetti essential oils isolated from wood tar and sawdust

The present research was devoted to evaluating the effect of provenance and wood pyrolysis process on the phytochemical and antioxidant activity of essential oils extracted from sawdust and tar of Cedrus atlantica Manetti of Morocco. The essential oils were obtained by hydro-distillation from Cedar wood growing in two geographical locations of the Middle Atlas of Morocco (Senoual and Itzer forests) using a Clevenger-type apparatus and analyzed by Gas Chromatography-Mass spectrometry (GC/MS). Seventy compounds were approximately identified for each essential oil, accounting for 94% of the total oil’s composition, with the predominance of sesquiterpene hydrocarbons, where, α-himachalene (13.75%, 1.15%, 12.2%, and 16.69%) and β-himachalene (24.05%, 24.25%, 27.67%, and 44.23%) represented the major constituents in the four essential oils obtained. Multivariate analysis was used to discriminate the essential oils using principal component analysis (PCA) and Hierarchical Clustering Analysis (HCA). In addition, heatmap for dendrogram was used to investigate any correlation between the chemical profiles of each essential oil. Moreover, the antioxidant properties of the essential oils were studied using DPPH scavenging and Ferric Ion Reducing Power (FRAP). The results indicate that the essential oils from wood tar of Cedrus atlantica possess a strong antioxidant activity (IC₅₀ = 0.126 mg/mL and 0.143 mg/mL) in comparison with those from sawdust (IC₅₀ = 15.6 mg/mL and 16.3 mg/mL).     

Antioxidant activity and cytotoxicity on tumour cells of the essential oil from Cedronella canariensis var. canariensis (L.) Webb & Berthel. (Lamiaceae)

Cedronella canariensis is a lemon-scented species of the family Lamiaceae endemic to the Canary Islands where it is used in the traditional medicine to prepare infusions or inhalations for anti-catarrhal, tonic, diuretic, hypoglycaemiant, hypotensive, anti-inflammatory and decongestant of the respiratory tract. In this work we investigated for the first time the antioxidant activity of the essential oil and its inhibitory effects on tumour cells (A375, MDA-MB-231, HCT 116) proliferation by DPPH, ABTS, FRAP and MTT assays, respectively. The oil, analysed by GC-ionisation flame detector and GC–MS, was characterised by pinocarvone (58.0%) and β-pinene (10.8%) as the major constituents, being typical of the chemotype ‘canariensis’. Noteworthy was the cytotoxic activity of the oil against the tumour cells examined, with IC₅₀ values of 4.3, 7.3 and 11.4 μg/mL on A375, MDA-MB-231 and HCT 116 tumour cells, respectively, as well as the scavenging activity against the ABTS radical (IC₅₀ of 10.5 μg/mL).