Chemotyping of diverse Eucalyptus species grown in Egypt and antioxidant and antibacterial activities of its respective essential oils

The chemical composition of the essential oil from the leaves of Eucalyptus camaldulensis, Eucalyptus camaldulensis var. obtusa and Eucalyptus gomphocephala grown in northern Egypt was analysed by using GC-FID and GC–MS techniques. The antibacterial (agar disc diffusion and minimum inhibitory concentration methods) and antioxidant activities (2,2′-diphenypicrylhydrazyl) were examined. The main oils constituents were 1,8-cineole (21.75%), β-pinene (20.51%) and methyleugenol (6.10%) in E. camaldulensis; spathulenol (37.46%), p-cymene (17.20%) and crypton (8.88%) in E. gomphocephala; spathulenol (18.37%), p-cymene (19.38%) and crypton (16.91%) in E. camaldulensis var. obtusa. The essential oils from the leaves of Eucalyptus spp. exhibited considerable antibacterial activity against Gram-positive and Gram-negative bacteria. The values of total antioxidant activity were 70 ± 3.13%, 50 ± 3.34% and 84 ± 4.64% for E. camaldulensis, E. camaldulensis var. obtusa and E. gomphocephala, respectively. The highest antioxidant activity value of 84 ± 4.64% could be attributed to the high amount of spathulenol (37.46%).     

Composition and antioxidant activity of Senecio nudicaulis Wall. ex DC. (Asteraceae): a medicinal plant growing wild in Himachal Pradesh,India

The composition of essential oil isolated from Senecio nudicaulis Wall. ex DC. growing wild in Himachal Pradesh, India, was analysed, for the first time, by capillary gas chromatography (GC) and GC–mass spectrometry. A total of 30 components representing 95.3% of the total oil were identified. The essential oil was characterised by a high content of oxygenated sesquiterpenes (54.97%) with caryophyllene oxide (24.99%) as the major component. Other significant constituents were humulene epoxide-II (21.25%), α-humulene (18.75%), β-caryophyllene (9.67%), epi-α-cadinol (2.90%), epi-α-muurolol (2.03%), β-cedrene (1.76%), longiborneol (1.76%), 1-tridecene (1.16%) and citronellol (1.13%). The oil was screened for antioxidant activity using DPPH, ABTS and nitric oxide-scavenging assay. The oil was found to exhibit significant antioxidant activity by scavenging DPPH, ABTS and nitric oxide radicals with IC₅₀ values of 10.61 ± 0.14 μg mL^? 1, 11.85 ± 0.28 μg mL^? 1 and 11.29 ± 0.42 μg mL^? 1, respectively.     

Headspace Solid Phase Microextraction for Terpenes and Volatile Compounds Determination in Mastic Gum Extracts,Mastic Oil and Human Urine by GC– MS

A reliable analytical method was developed, which is based on Headspace Solid Phase Microextraction (HS-SPME) and Gas Chromatography–Mass Spectrometry (GC-MS) for the detection of volatile components of the gum and the essential oil of Pistacia lentiscus var. chia, commonly known as mastic gum and mastic oil respectively. The conditions of the HS-SPME were optimized and aqueous-ethanolic extracts of mastic gum and solutions of mastic oil in ethanol-water were analyzed by GC-MS. Almost 26 volatile components in mastic gum and 34 in mastic oil were identified in the gum and the oil respectively. The major constituents of the mastic gum and the mastic oil were α-pinene (63% and 76%, respectively), β-myrcene (15% and 14%), β-pinene (4% and 4%), limonene (2.5% and 1.5%), and caryophyllene (5% and 1%). The quantitative determination of six of the aforementioned substances in multi-analyte standard solutions was achieved with good performance features. The repeatability (RSD%) was <4.2% and the limits of detection were 1.2 µg/L for α-pinene, 0.09 µg/L for β-pinene, 0.7 µg/L for β-myrcene, 0.02 µg/L for camphene, 0.02 µg/L for p-cymene, and 0.07 µg/L for α-terpineol. The HS-SPME/GC-MS procedure was successfully applied to samples of human urine samples after dietetic use of various mastic products such as mastic gum, mastic oil and Greek traditional highly viscous white mastic sweet. Traces of several constituents of mastic, such as α-pinene, β-myrcene, limonene, p-methyl anisole, terpinene, carveol, myrtenol, caryophyllene, α-caryophyllene, and so forth, were detected in the collected urine samples.     

Senna occidentalis (L.) Link and Senna hirsuta (L.) H. S. Irwin & Barneby: constituents of fruit essential oils and antimicrobial activity

Senna occidentalis and S. hirsuta are mostly gathered from the wild for medicinal use and have a disagreeable odour when crushed. The volatile oils isolated from fresh fruits of S. occidentalis and S. hirsuta were subjected to gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS) and antimicrobial assays. GC and GC-MS analyses permitted the identification of 58 constituents. S. occidentalis oil was dominated by cyperene (10.8%), β-caryophyllene (10.4%), limonene (8.0%) and caryophyllene oxide (6.8%). The main components of S. hirsuta fruit oil were benzyl benzoate (24.7%), τ-cadinol (18.9%), 2,5-dimethoxy-p-cymene (14.6%) and β-caryophyllene (5.1%). S. occidentalis fruit oil exhibited better antimicrobial activity (MIC 78–312 μg/mL) against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Aspergillus niger compared with S. hirsuta oil. The compositions and the activities of the fruit essential oils of S. occidentalis and S. hirsuta are reported for the first time.     

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.     

Chemical composition and biological activities of Iranian Achillea wilhelmsii L. essential oil: a high effectiveness against Candida spp. and Escherichia strains

In the case of Achillea wilhelmsii, 30 compounds were identified representing 94.48% of the total oil with a yield of 0.82% w/w. The major constituents of the oil were described as α-thujene (6.11%), α-pinene (5.11%), sabinene (5.23%), p-cymene (7%), 1,8-cineole (6%), linalool (10%), camphor (8.43%), thymol (18.98%) and carvacrol (20.13%). A. wilhelmsii oil exhibited higher antibacterial and antifungal activities with a high effectiveness against Escherichia coli and Candida albicans with the lowest minimum inhibitory concentration and minimum bactericidal concentration/minimum fungicidal concentration value (2 ± 0.0–2 ± 0.0 g/mL, 1 ± 0.5–1 ± 0.5 g/mL), respectively. Results showed that A. wilhelmsii oil exhibits a higher activity in each antioxidant system with a special attention for β-carotene bleaching test (IC₅₀: 19 μg/mL) and reducing power (EC₅₀: 10 μg/mL). Antioxidant activity-guided fractionation of the oil was carried out by TLC-bioautography screening and fractionation resulted in the separation of main antioxidant compounds which were identified as thymol (65%) and carvacrol (19%). In conclusion, these results support the use of the essential oil and its main compounds for their antioxidant properties and antimicrobial activity.     

Chemical composition and antimicrobial activity of the essential oils from flowers and leaves of Grindelia integrifolia DC

Essential oils from flowers and leaves of Grindelia integrifolia DC. were investigated for the first time in terms of chemical composition and antimicrobial activity. The GC-FID/MS analysis allowed for the identification of 58 and 72 volatiles, comprising 92.4 and 90.1% of the oils, respectively. The major components of the flower oil were α-pinene (34.9%) and limonene (13.1%), while myrcene (16.9%), spathulenol (12.3%), β-eudesmol (11.9%) and limonene (10.1%) dominated among the leaf volatiles. The antimicrobial activity, evaluated against 12 selected bacteria and fungus, was found moderate, with the strongest effect of both oils observed against C. albicans (MIC = MBC: 0.63 and 0.31 mg/mL for flower and leaf oil, respectively).     

Chemical composition and antimicrobial activity of essential oils from Acantholippia deserticola,Artemisia proceriformis,Achillea micrantha and Libanotis buchtormensis against phytopathogenic bacteria and fungi

Essential oils from aerial parts of Acantholippia deserticola, Artemisia proceriformis, Achillea micrantha and Libanotis buchtormensis were analysed by GC–MS. The major compounds identified were β-thujone (66.5 ± 0.2%), and trans-sabinyl acetate (12.1 ± 0.2%) in A. deserticola; α-thujone (66.9 ± 0.4%) in A. proceriformis; 1,8-cineole (26.9 ± 0.5%), and camphor (17.7 ± 0.3%) in A. micrantha and cis-β-ocimene (23.3 ± 0.3%), and trans-β-ocimene (18.4 ± 0.2%) in L. buchtormensis. The oils showed a weak antimicrobial effect (MIC₁₀₀ > 1.5 mg/ml) on most phytopathogens tested. A moderate antimicrobial activity (MIC₁₀₀ between 0.5 and 1.5 mg/ml) was displayed by the oils of A. deserticola, A. micrantha and L. buchtormensis on Septoria tritici and by the oil of A. deserticola on Septoria glycine. The antimicrobial activity was associated to the contents of β-thujone, trans-sabinyl acetate and trans-sabinol. Our results indicate that the tested essential oils have little inhibitory potency not suitable for use as plant protection products against the phytopathogens assayed.     

Chemical composition and α-amylase inhibitory activity of the essential oil from Sabina chinensis cv. Kaizuca leaves

Sabina chinensis cv. Kaizuca (SCK) is a variant of S. chinensis L. The essential oil from its leaves exhibited α-amylase inhibitory activity in vitro and the IC₅₀ value was 187.08 ± 0.56 μg/mL. Nineteen compounds were identified from this essential oil by gas chromatography–mass spectrometry (GC-MS) analysis. The major compounds identified were bornyl acetate (42.6%), elemol (20.5%), β-myrcene (13.7%) and β-linalool (4.0%). In order to study the reason of the α-amylase inhibitory activity of this essential oil, the identified compounds were docked with α-amylase by molecular docking individually. Among these compounds, γ-eudesmol exhibited the lowest binding energy (?6.73 kcal/mol), followed by α-copaen-11-ol (?6.66 kcal/mol), cubedol (?6.39 kcal/mol) and α-acorenol (?6.12 kcal/mol). The results indicated that these compounds were the active ingredients responsible for the α-amylase inhibitory activity of essential oil from SCK.     

Chemical composition,antimicrobial and antioxidant activities of the essential oil of Psammogetoncanescens

This study reports the chemical composition, antimicrobial activity and antioxidant properties of Psammogeton canescens essential oil (EO) and its main compounds. The EO was obtained from the aerial parts of P. canescens by hydrodistillation and analysed by using GC/MS. The main constituent was β-bisabolene (25%), followed by α-pinene (20%), apiole (15.34%), γ-terpinene (7.34%), p-cymene (5.35%), β-pinene (5.41%), camphene (5.12%), dill apiole (5%), myrcene (4.54%), colchicine (0.56), sylvestrene (0.56%), β-caryophyllene (0.45%), caryophyllene oxide (0.43%), (Z)-β-farnesene (0.32%), cembrene (0.21%), folic acid (0.21%), germacrene D (0.14) and β-sesquiphellandrene (0.13). β-Bisabolene exhibited strong antioxidant activity (14 ± 0.8 μg/mL). The EO of P. canescens was particularly active against Candida albicans and Escherichia coli, with the lowest minimum inhibitory concentration and minimum bactericidal/fungicidal concentration values. In conclusion, these results support the use of the EO and its main compounds for their antioxidant properties and antimicrobial activity.     

Essential oil extraction,chemical analysis and anti-Candida activity of Foeniculum vulgare Miller – new approaches

A comprehensive study on essential oil samples of Foeniculum vulgare Miller from Tarquinia (Italy) is reported. A 24-h systematic steam distillation was performed on different harvested samples applying different extraction times. The GC-MS analysis of the residue outcome showed o-cymene, α-phellandrene, α-pinene and estragole as the major constituents. The predominance and continued presence of o-cymene makes this fennel oil a rather unique chemotype. An evident correlation between the antifungal activity and phenological stage is demonstrated. The most active fractions were particularly rich in estragole, as well as a significant amount of fenchone that possibly exerts some additive effect in the expression of overall antifungal potency. Pre-fruiting material produced oil particularly rich in o-cymene. With reference to the duration of the extraction, the maximum amount of oil was released within the first 3 h, whereas the reproductive phase material needed at least 6 h for the extraction.     

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.     

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.     

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 constituents of essential oil of endemic Rhanterium suaveolens Desf. growing in Algerian Sahara with antibiofilm,antioxidant and anticholinesterase activities

Twenty compounds were detected in the essential oil of Rhanterium suaveolens representing 98.01% of the total oil content. Perillaldehyde (45.79%), caryophyllene oxide (24.82%) and β-cadinol (5.61%) were identified as the main constituents. In β-carotene–linoleic acid assay, both the oil and the methanol extract exhibited good lipid peroxidation inhibition activity, with IC₅₀ values of 17.97 ± 5.40 and 11.55 ± 3.39 μg/mL, respectively. In DPPH and CUPRAC assays, however, the methanol extract exhibited a good antioxidant activity. The highest antibiofilm activity has been found 50.30% against Staphylococcus epidermidis (MU 30) at 20 μg/mL for essential oil and 58.34% against Micrococcus luteus (NRRL B-4375) at 25 mg/mL concentration for methanol extract. The in vitro anticholinesterase activity of methanol extract showed a moderate acetylcholinesterase inhibitory (IC₅₀ = 168.76 ± 0.62 μg/mL) and good butyrylcholinesterase inhibitory (IC₅₀ = 54.79 ± 1.89 μg/mL) activities. The essential oil was inactive against both enzymes.     

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.     

Chemical composition,antioxidant and antimicrobial activity of the essential oil from the leaves of Macleaya cordata (Willd) R. Br.

The essential oil from the leaves of Macleaya cordata R.Br. obtained by hydrodistillation was analysed by gas chromatography/mass spectrometry. Sixty-eight compounds consisting of up to 92.53% of the essential oil were identified. Antioxidant activities of the essential oil were evaluated by using DPPH radical scavenging and β-carotene–linoleic acid assays. The essential oil showed moderate antioxidant activity. In addition, the essential oil exhibited potential antimicrobial activity against all tested microorganisms, with diameters of inhibition zones ranging from 8.7 ± 0.5 to 17.2 ± 1.2 mm and minimum inhibitory concentration values from 125 to 500 μg/mL. We selected the most sensitive bacterium Staphylococcus aureus as model to observe of the action of essential oils of M. cordata on the membrane structure by scanning electron microscopy. The treated cell membranes were damaged severely. The results presented here indicate that the essential oil of M. cordata may be potential sources of antioxidant and antimicrobial agents in the future.     

Phenolic profile,antioxidant capacity and anti-inflammatory activity of Anethum graveolens L. essential oil

This study reports the chemical composition, antioxidant and anti-inflammatory properties of Anethum graveolens essential oil and its main compounds. The essential oil was obtained from the aerial parts of the plant by hydrodistillation and analysed by using GC/MS. α-Phellandrene (19.12%), limonene (26.34%), dill ether (15.23%), sabinene (11.34%), α-pinene (2%), n-tetracosane (1.54%), neophytadiene (1.43%), n-docosane (1.04), n-tricosane (1%), n-nonadecane (1%), n-eicosane (0.78%), n-heneicosane (0.67%), β-myrcene (0.23%) and α-tujene (0.21%) were found to be the major constituents of the oil. A. graveolens oil exhibit a higher activity in each antioxidant system with a special attention for β-carotene bleaching test (IC₅₀: 15.3 μg/mL) and reducing power (EC₅₀: 11.24 μg/mL). The TLC-bioautography screening and fractionation resulted in the separation of the main antioxidant compounds, which were identified as limonene (45%) and sabinene (32%). The essential oil and its main compounds exhibited a potent NO-scavenging effect and inhibited the expression of inducible NO synthase.     

A study on the seasonal variation of the essential oil composition from Plectranthus hadiensis and its antibacterial activity

The chemical composition and seasonal variation of the essential oil from the aerial parts of Plectranthus hadiensis grown during the rainy and summer seasons in the Western Ghats of India was analysed by GC–MS technique. The analysis of rainy season oil led to the identification of 31 compounds, representing 96.4% of the essential oil and the winter season oil led to 25 compounds, representing 95.1% of the oil. Most of the compounds were sesquiterpenes and oxygenated monoterpenes. The major components of the rainy season oil were L-fenchone (30.42%), β-farnesene (11.87%), copaene(11.10%), 2,3-dimethyl hydroquinone (10.78%), α-caryophyllene(8.41%) and piperitone oxide (3.94%) and of the summer season oil are L-fenchone (31.55%), copaene(11.93%), β-farnesene (10.45%), 1,8-naphthalenedione, 8a-ethylperhydro (10.06%), α-caryophyllene(6.36%), piperitone oxide (5.79%) and limonene(4.63%). Antibacterial activity of the essential oil of P. hadiensis was tested using zone of inhibition and minimum inhibition concentration methods. Both the oils inhibited the organisms and showed the zone of inhibition in the range of 20–35 mm with MIC values between 32 and 64 mg/dL.     

Seasonal variations of volatile constituents of Hemizygia bracteosa (Benth.) Briq. aerial parts from Benin

Essential oils from fresh aerial parts of Hemizygia bracteosa (Benth.) Briq. were extracted by steam distillation. The oil yield from plants collected during the hot season (February) and during the cold season (August) were 0.12 ± 0.01% and 0.25 ± 0.02%, respectively. GC/FID and GC/MS analyses allowed us to identify a total of 65 compounds, representing 97% of the hydrodistillate. The main components of the oil from the hot period were (E)-β-farnesene (64 ± 0.04%), β-elemene (7.4 ± 0.05%), trans-nerolidol (6.2 ± 0.04%), and α-muurolene (2.7 ± 0.03%). The essential oil from the cold season was characterized by the presence, as major compounds, of (E)-β-farnesene (67 ± 0.04%) along with β-caryophyllene (3.6 ± 0.06%), β-elemene (3.3 ± 0.05%), 7-epi-α-selinene (3.1 ± 0.01%) and p-cymene (2.5 ± 0.04%). This is the first report of these components in the essential oil of Hemizygia bracteosa (Benth.) Briq.