Investigation of the chemical composition–antibacterial activity relationship of essential oils by chemometric methods

The antibacterial effects of Thymus vulgaris (Lamiaceae), Lavandula angustifolia (Lamiaceae), and Calamintha nepeta (Lamiaceae) Savi subsp. nepeta var. subisodonda (Borb.) Hayek essential oils on five different bacteria were estimated. Laboratory control strain and clinical isolates from different pathogenic media were researched by broth microdilution method, with an emphasis on a chemical composition–antibacterial activity relationship. The main constituents of thyme oil were thymol (59.95%) and p-cymene (18.34%). Linalool acetate (38.23%) and β-linalool (35.01%) were main compounds in lavender oil. C. nepeta essential oil was characterized by a high percentage of piperitone oxide (59.07%) and limonene (9.05%). Essential oils have been found to have antimicrobial activity against all tested microorganisms. Classification and comparison of essential oils on the basis of their chemical composition and antibacterial activity were made by utilization of appropriate chemometric methods. The chemical principal component analysis (PCA) and hierachical cluster analysis (HCA) separated essential oils into two groups and two sub-groups. Thyme essential oil forms separate chemical HCA group and exhibits highest antibacterial activity, similar to tetracycline. Essential oils of lavender and C. nepeta in the same chemical HCA group were classified in different groups, within antibacterial PCA and HCA analyses. Lavender oil exhibits higher antibacterial ability in comparison with C. nepeta essential oil, probably based on the concept of synergistic activity of essential oil components.     

Antibacterial activity and GC/MS analysis of the essential oils from flower, leaf and stem of Origanum vulgare ssp. viride growing wild in north-west Iran

Essential oils obtained from flowers, leaves and stems of Origanum vulgare L. ssp. viride (Boiss.) Hayek., growing wild in Ardabil Province (north-west Iran), were analyzed by GC and GC/MS. beta-Caryophyllene was the major constituent in all three oils (48.1%, 50.1% and 60.2%, respectively). Of the 19 components detected in the flower oil, comprising 96.3% of the total, the major components were 1,8-cineole (11.6%), alpha-pinene (6.9%), and gamma-cadinene (4.8%). 1-Octen-3-ol (23.8%), and 1,8-cineole (8.5%) predominated in the leafoil. In the stem oil, other main constituents were bicyclogermacrene (9.8%), 1,8-cineole (6.4%), borneol (5.1%), and pinocarvone (4.4%). The essential oils were evaluated for their antibacterial activity against 10 selected microorganisms. The data obtained contribute to the future use of certain essential oils as natural preservatives for food products, due to their safety and positive effect on shelf life.     

Anthemis cotula L. from Jordan: Essential oil composition,LC-ESI-MS/MS profiling of phenolic acids - flavonoids and in vitro antioxidant activity

Essential oils of the leaves and flowers of Anthemis cotula L. (family Asteraceae) grown in Jordan were extracted by hydro-distillation and then analyzed by GC–MS. Sesquiterpenes hydrocarbons (SH) were the dominant components in the oils extracted from leaves and flowers of A. cotula. γ-Muurolene and aromadendrene, were the major compounds that were obtained from the flowers oil, while γ-muurolene and trans-cadinene ether were detected as major ingredients in the leaves extract. LC-MS analysis was carried out to identify the significant compounds from each extract. Additionally, butanol (B), aqueous methanol (M) and water (W) extracts prepared from the flowers and the leaves of A. cotula were analysed by LC-MS/MS. Apigenin and chlorogenic acid were the main constituents detected in the flowers’ alcoholic extracts and leaves’ aqueous extract. Moreover, the essential oils and all prepared extracts were assayed for their total antioxidant activity using the DPPH, ABTS, and ferrous ion chelating effect (FIC) assay methods. All investigated oils and extracts showed interesting activity as compared to the positive controls employed (α-tocopherol and ascorbic acid).     

The Impact of Selected Essential Oils Applied to Non-Woven Viscose on Bacteria That Cause Lower Urinary Tract Infections—Preliminary Studies

Inflammation of the lower urinary tract is a very common problem, which occurs particularly in women. A concept of a biotextronics system for preventive and support treatment of lower urinary tract inflammations was presented. The system includes a non-woven viscose insert for essential oils application. The oils were deposited on the non-woven viscose and incubated in the temperature of 37 °C and served a model for their action in the vapor phase as the element of the biotextronics system. The essential oils used in the research were the following: chamomile (Matricaria chamomilla L.), sage (Salvia officinalis L. and Salvia lavandulaefolia), juniper (Juniperus communis L.), thyme (Thymus vulgaris L.), and mixtures of chamomile oil with oils of each sage species in a 1:1 ratio. The oils were tested against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus epidermidis, Staphylococcus saprophyticus, and Enterococcus faecalis. The best inhibitory effect in vapor phase was noted for chamomile essential oil at the lowest concentration (0.054 µL/cm³). Both mixtures of chamomile and sage acted antagonistically, lowering the antibacterial activity of the individual oils applied solely. Juniper and Salvia officinalis essential oils at the concentrations tested increased the growth of at least one of the bacteria tested. Salvia lavandulaefolia Vahl. essential oil inhibited all bacteria, only at the concentration 0.214 µL/cm³. The thyme oil, at the concentration 0.054 µL/cm³, reduced the growth of all bacterial species tested. Chamomile and thyme essential oils were chosen for further research in the biotextronics pantiliner system.     

Phytochemical screening and biological activities of the oil components of Prunus domestica Linn

Phytochemical screening of three different oil fractions, obtained from n-hexane extract of Prunus domestica shoots were analyzed by GC and GC–MS. It resulted in the identification of 9, 16 and 24 compounds which representing 92.56%, 90.6% and 90.69% of these oil fractions, respectively. The main components identified from fraction 1, 2 and 3 were hentricontane (35.7%), ethyl hexadecanoate (21.7%) and linoleic acid (16.16%), respectively. Bioassay screening of oil showed moderate antibacterial activity against Salmonella group (Gram +ve and ?ve) by agar well diffusion method, moderate antifungal activity against Microsporum canis by agar tube dilution method and good antioxidant activity by DPPH radical scavenging method.     

Impact of Altitudinal Variation on the Phytochemical Profile,Anthelmintic and Antimicrobial Activity of Two Pinus Species

Active components from natural sources are the current focus in most pharmacological research to provide new therapeutic agents for clinical use. Essential oils from the Pinus species have been traditionally used in medicine. This study aimed to investigate the chemical profile of two Pinus species, Pinus halepensis L. and Pinus pinea Mill, from different altitudes in Libya and study the effect of environmental conditions on the biological activities of essential oils. A clevenger apparatus was used to prepare the essential oils by hydrodistillation. Analyses were done using GC/MS. Anthelmintic and antimicrobial activities were tested against the earthworm Allolobophora caliginosa, gram-positive bacteria, gram-negative bacteria, and fungi. Different chemical profiles were observed among all tested essential oils, and terpenes were the most dominant class. All studied essential oils from the Pinus species exhibited a remarkable anthelmintic activity compared to the standard piperazine citrate drug. Pinus halepensis from both altitudes showed broad-spectrum antimicrobial activity against all tested microorganisms, while Pinus pinea was effective against only Escherichia coli. From these findings, one can conclude that there are variations between studied species. The essential oil compositions are affected by environmental factors, which consequently affect the anthelmintic and antimicrobial activity.     

Chemical composition and antimicrobial activities of the essential oil of (Tunisian) Chrysanthemum trifurcatum (Desf.) Batt. and Trab. flowerheads

The chemical composition of essential oil isolated from the flowerheads of Chrysanthemum trifurcatum (Desf.) Batt. and Trab. var. macrocephalum (viv.) Beg. (Asteraceae) by hydrodistillation was analysed by GC and GC/MS. A total of 56 compounds representing 97.48% of the oil were identified: limonene (20.89%), γ-terpinene (19.13%), 1,8-cineole (10.64%), β-pinene (8.77%), α-pinene (5.32%), 2-hexenal (4.85%), 4-terpenyl acetate (3.42%), β-myrcene (2.31%), germacrene-B (2.01%), β-spathulenol (1.62%), longifolene (1.39%), α-cadinol (1.39%), α-thujene (1.23%) and β-bourbobene (1.06%) were found to be the major components. Essential oil of flowerheads of C. trifurcatum was tested for antibacterial activity against eight strains, using a microdilution method, and for cytotoxicity and antiviral activity against Herpes simplex virus type 1 using a neutral red incorporation method. The oil showed a great potential of antibacterial effect against Staphylococcus epidermidis and Bacillus subtilis, in the inhibition range of 64–66% and IC₅₀ ranging from 62.5 to 125 μg/ml. On Vero cells, the CC₅₀ of the oil was 735.9 μg/ml and it did not exhibit a significant antiviral activity.     

Chemical composition of the essential oil of Moluccella spinosa L. (Lamiaceae) collected wild in Sicily and its activity on microorganisms affecting historical textiles

In this study the chemical composition of the essential oil from aerial parts of Moluccella spinosa L. collected in Sicily was evaluated by GC and GC-MS. The main components of M. spinosa L. were α-pinene (26.6%), caryophyllene oxide (16.8%) and β-caryophyllene (8.6%). A comparison with other studied oils of genus Moluccella is made. Antibacterial and antifungal activities against some microorganisms infesting historical textiles were also determined.     

Synthesis,characterization and antimicrobial activity evaluation of new 2,4-Thiazolidinediones bearing imidazo[2,1-b][1,3,4]thiadiazole moiety

The synthesis and antimicrobial activity of 2,4-thiazolidinedione derivatives 5a–g and 6a–g are described. The structures of the newly synthesized compounds were confirmed by IR, NMR, mass and elemental analyses. All compounds were evaluated for their preliminary in vitro antibacterial and antifungal activity. The results revealed that most of the compounds showed high or moderate biological activity against tested microorganisms.     

Commercial Origanum compactum Benth. and Cinnamomum zeylanicum Blume essential oils against natural mycoflora in Valencia rice

Chemical composition of commercial Origanum compactum and Cinnamomum zeylanicum essential oils and the antifungal activity against pathogenic fungi isolated from Mediterranean rice grains have been investigated. Sixty-one compounds accounting for more than 99.5% of the total essential oil were identified by using gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Carvacrol (43.26%), thymol (21.64%) and their biogenetic precursors p-cymene (13.95%) and γ-terpinene (11.28%) were the main compounds in oregano essential oil, while the phenylpropanoids, eugenol (62.75%), eugenol acetate (16.36%) and (E)-cinnamyl acetate (6.65%) were found in cinnamon essential oil. Both essential oils at 300 μg/mL showed antifungal activity against all tested strains. O. compactum essential oil showed the best antifungal activity towards Fusarium species and Bipolaris oryzae with a total inhibition of the mycelial growth. In inoculated rice grains at lower doses (100 and 200 μg/mL) significantly reduced the fungal infection, so O. compactum essential oil could be used as ecofriendly preservative for field and stored Valencia rice.     

Variation in the Antibacterial and Antioxidant Activities of Essential Oils of Five New Eucalyptus urophylla S.T. Blake Clones in Thailand

Eucalyptus oils are widely used for a variety of purposes. This study investigates the terpenoid compositions and antibacterial and antioxidant activities of eucalypt leaf oils extracted from four E. urophylla clones and one E. urophylla × E. camaldulensis hybrid clone grown in Thailand. According to GC/MS analysis, the E. urophylla oils were mainly composed of 1,8-cineole, α-terpinyl acetate, β-caryophyllene, and spathulenol, while 1,8-cineole, α-terpinyl acetate, p-cymene, and γ-terpinene were mostly identified in the hybrid oil. All eucalypt oils exhibited a significant bacteriostatic effect against Gram-positive bacteria, Streptococcus pyogenes, Staphylococcus aureus, Listeria monocytogenes, and Bacillus cereus. Only the hybrid oil had an effect on all Gram-negative bacteria tested, including Salmonella typhi, Escherichia coli, Pseudomonas aeruginosa, and Enterobacter aerogenes. These oils have antibacterial properties that vary according to their terpenoid content. Only the hybrid oil had a potent antioxidant effect, with an IC₅₀ value of 4.21 ± 0.35 mg/mL for free radical (DPPH) scavenging. This oil’s antioxidant effect may be a result of the phenolic terpenoids, thymol and carvacrol. As a result, these oils may be a novel source of antibacterial and antioxidant agents. Additionally, the antibacterial and antioxidant capabilities of the E. urophylla × E. camaldulensis hybrid essential oil are reported for the first time.     

Chemical composition of essential oils of Anthemis secundiramea Biv. subsp. secundiramea (Asteraceae) collected wild in Sicily and their activity on micro-organisms affecting historical art craft

Abstract

In the present study, the chemical composition of the essential oil from the aerial parts of Anthemis secundiramea Biv. subsp. secundiramea L. collected in Sicily was evaluated by GC and gas chromatography–mass spectrometry. The main components of A. secundiramea were (Z)-lyratyl acetate (14.6%), (Z)-chrysanthenyl acetate (9.9%), (Z)-chrysanthenol (8.7%) and (E)-chrysanthenyl acetate (7.7%). The comparing with other studied oils of genus Anthemis belonging to the same clade is discussed. Antibacterial and antifungal activities against some micro-organisms infesting historical art craft, were also determined.     

Chemical composition of the essential oils of Centaurea tomentella Hand.-Mazz. and C. haussknechtii Boiss. (Asteraceae) collected wild in Turkey and their activity on microorganisms affecting historical art craft

In the present study the chemical composition of the essential oils from aerial parts of Centaurea tomentella Hand.-Mazz. and C. haussknechtii Boiss. collected in Turkey was evaluated by GC and GC-MS. The main components of C. tomentella L. were hexadecanoic acid (19.7%), caryophyllene oxide (6.6%) and spathulenol (4.8%) whereas C. haussknechtii was rich in hexadecanoic acid (26.2%), (Z,Z)-9,12-octadecadienoic acid (19.3%), heptacosane (5.3%) and nonacosane (5.1%). Antibacterial and antifungal activities against some microorganisms infesting historical art craft, were also determined.     

Cytotoxic tropolones from the fungus Nemania sp. BCC 30850

Twelve new compounds, including nine tropolones, nemanolones A?I (1–9), three 7-isochromenones, nemanecins A?C (10–12), and a new naturally isolated 4-isochromanone (13), along with two known compounds, 7,8-dihydroxy-3-methyl isochroman-4-one (XJP), and chaetoquadrin F, were isolated from culture broth of the fungus Nemania sp. BCC 30850. Structures of these compounds were elucidated by NMR and MS spectroscopic analyses. Nemanolones exhibited cytotoxic activities and two of them, compounds 1 and 2, also showed antibacterial activity against Bacillus cereus and antifungal activity against Candida albicans.     

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.     

Chemical composition and evaluation of the antimicrobial activity of the essential oil from leaves of Eugenia platysema

This study describes the qualitative and quantitative chemical composition and evaluates the antibacterial activity of essential oil from Eugenia platysema leaves. Analysis by GC–FID and GC–MS allowed the identification of 22 compounds. Different from the other species of the Eugenia genus, the major compound found in the essential oil was the diterpene phytol (66.05%), being this the first report of the presence of this compound in the essential oils from Eugenia genus. The sesquiterpene elixene was the second most concentrated compound in the studied essential oil (9.16%). The essential oil from E. platysema was tested for its antibacterial activity against cell-walled bacteria and mollicute strains of clinical interest using the microdilution broth assay. The results showed that the essential oil of E. platysema was inactive until 1000 μg mL^?1 against tested bacteria.     

Effect of Extraction Methods on Polyphenols,Flavonoids, Mineral Elements,and Biological Activities of Essential Oil and Extracts of Mentha pulegium L.

Our study evaluated the in vitro antioxidant properties, antibacterial and antifungal activities, anti-inflammatory properties, and chemical composition of the essential oils (EOs), total phenol, and total flavonoid of wild Mentha pulegium L. This study also determined the mineral (nutritional and toxic) elements in the plant. The EOs were extracted using three techniques—hydro distillation (HD), steam distillation (SD), and microwave-assisted distillation (MAD)—and were analyzed using chromatography coupled with flame ionization (GC-FID) and gas chromatography attached with mass spectrometry detector (GC-MS). The antioxidant effects of the EOs were tested with 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ABTS (2,2’-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), while the antibacterial and antifungal activities of the EO and methanolic extract were tested using Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, Escherichia coli, and Candida albicans. Twenty-six compounds were identified in the essential oil, representing 97.73% of the total oil, with 0.202% yield. The major components were pulegone (74.81%), menthone (13.01%) and piperitone (3.82%). Twenty-one elements, including macro- and micro-elements (Ba, Br, Ca, Cl, Co, Cr, Cs, Eu, Fe, K, Mg, Mn, Mo, Na, Rb, Sb, Sc, Sr, Th, U and Zn), were detected using neutron activation analysis (INAA) and inductively coupled plasma optical emission spectrometry (ICP-OES), with the concentration of mineral element close to the FAO recommendation. The results show that the EOs and extracts from Mentha pulegium L. had significant antimicrobial activities against the microorganisms, including five human pathogenic bacteria, one yeast (Candida albicans), and one phytopathogenic fungi. The in vivo anti-inflammatory activities of the leaf extracts were confirmed. The results indicate that the EOs and extracts from Mentha pulegium L. have promising applications in the pharmaceutical industries, clinical applications, and in medical research.     

Chemical composition and antimicrobial activity of the essential oils of Artemisia absinthium,Artemisia scoparia,and Artemisia sieberi grown in Saudi Arabia

Essential oils (EOs) are one of the most significant products of plant metabolites, the current research work was performed to determine and compare the chemical compositions of the EOs extracted from three different species of Artemisia (absinthium, sieberi, and scoparia) growing in Saudi Arabia and to test their antimicrobial potential against different bacterial and fungal strains. The EOs were isolated by hydro-distillation and analyzed by combining a gas chromatography–flame ionization detector (GC–FID) with the gas chromatography–mass spectroscopy (GC–MS) technique. Chemical analysis revealed that the three species had four compounds in common, i.e., limonene, camphor, terpinen-4-ol, and ethyl 2-methylbutyrate, while the main components identified in the EOs of A. absinthium and A. sieberi were cis-davanone (34.7% and 36.1%, respectively) and camphor (16.2% and 24.1%, respectively). In contrast, the keto compounds dominated in the oil of A. scoparia with 2-nonanone (55%) and 2-undecanone (24.5%) representing more than 80% of the total oil content. In addition, the antimicrobial activity of the isolated oils was evaluated by the broth microdilution method, revealing that all the EOs isolated from the examined Artemisia species displayed growth inhibiting actions in a concentration-dependent manner on selected tested microorganism species. The findings of the study also suggested that the tested EOs could be used to develop effective natural antimicrobial remedies with potential application in the fields of cosmetic industry, food manufacturing and medicine.     

Synthesis of some Mannich base derivatives and their antimicrobial activity study

A series of 2-(phenyl)-2-(morpholin-4-yl)-N-phenylacetamide I–VII were synthesized by Mannich base method. Synthesized compounds I–VII were confirmed by IR, ¹H NMR, ¹³C NMR, mass and elemental analyses. Synthesized compounds I–VII were screened for antibacterial activity against various bacterial strains and compared with standard Ciprofloxacin at concentration 100 μg/mL and for antifungal activity against various fungal strains and compared with Clotrimazole at concentration 100 μg/mL; particularly 3-(4-chlorophenyl)-3-(morp holin-4-yl)-N-phenylpropanamide lll that has high antibacterial activity against Streptococcus epidermidis was compared with standard Ciprofloxacin.     

Composition of essential oil of lemon thyme (Thymus × citriodorus) at different hydrodistillation times

Distillation time can both to optimise the production and to engineer the composition of essential oil in essential oil bearing plants. Purpose of this study was to evaluate the effect of duration of hydrodistillation on composition of essential oil of Thymus × citriodorus, the natural source of commercially important geraniol and citral, a component with valuable biological properties. Essential oils were isolated by hydrodistillation at different distillation times and analysed by GC/MS analytical methods. Increase in percentage of essential oil during all hydrodistillation time gradient was uneven. Elongation of hydrodistillation time decreased percentages of monoterpenes but increased percentages of sesquiterpenes in essential oil. Results showed that the hydrodistillation of essential oil from lemon thyme longer than 60 min is useless.