Chemical diversity in curry leaf (Murraya koenigii) essential oils

Wild and cultivated Murraya koenigii leaf essential oils collected from ten Indian locations were investigated for their chemical diversity. The essential oil yields ranged from 1.2–2.5 ml/kg biomass. GC and GC-MS analyses revealed ninety compounds, constituting 93.8–99.9% of the essential oils. The highest concentrations of α-pinene (55.7%) and β-pinene (10.6%) were found in the essential oil of wild plants. α-Pinene (13.5–35.7%) and/or β-phellandrene (14.7–50.2%) were the dominant essential oil constituents of seven locations. (E)-Caryophyllene (26.5%, 31.5%) and α-selinene (9.5%, 10.4%) were the principal essential oil components of two locations. The odour profiles of the essential oils were distinctly different. Tetradecanoic acid, hexadecanoic acid, piperitone, cada-1,4-diene,1,10-di-epi-cubenol, γ-eudesmol, α-muurolol, (Z,E)-farnesol and (Z,Z)-farnesol are identified for the first time in curry leaf essential oil. The chemical diversity of the oils offers opportunity to flavourists to choose curry leaves and essential oils with preferential flavour composition.     

Comparative evaluation of the antibacterial activities of the essential oils of Rosmarinus officinalis L. obtained by hydrodistillation and solvent free microwave extraction methods

Rosmarinus officinalis L. is a perennial herb that belongs to the Lamiaceae family. It is used as a food flavouring agent, and well known medicinally for its powerful antimutagenic, antibacterial and chemopreventive properties. Essential oils were obtained from this plant by hydrodistillation (HD) and solvent free microwave extraction (SFME). GC–MS analyses of the oils revealed the presence of 24 and 21 compounds in the essential oils obtained through HD and SFME, respectively. The total yield of the volatile fractions obtained through HD and SFME was 0.31% and 0.39%, respectively. Higher amounts of oxygenated monoterpenes such as borneol, camphor, terpene-4-ol, linalool, α-terpeneol (28.6%) were present in the oil of SFME in comparison with HD (26.98%). However, HD oil contained more monoterpene hydrocarbons such as α-pinene, camphene, β-pinene, myrcene, α-phellanderene, 1,8-cineole, trans β-ocimene, γ-terpenene, and cis sabinene hydrate (32.95%) than SFME extracted oil (25.77%). The essential oils obtained using the two methods of extraction were active against all the bacteria tested at a concentration of 10 mg ml⁻¹. Minimum inhibitory concentration (MIC) values for all the susceptible bacteria ranged between 0.23 mg ml⁻¹ and 7.5 mg ml^−1.     

Chemical and biological characteristics of Cuminum cyminum and Rosmarinus officinalis essential oils

Essential oils extracted by hydrodistillation from Cuminum cyminum and Rosmarinus officinalis were characterized by means of GC and GC–MS. C. cyminum and R. officinalis contained α-pinene (29.1%, 14.9%), 1,8-cineole (17.9%, 7.43%) and linalool (10.4%, 14.9%), respectively, as the major compounds. C. cyminum oil exhibited stronger antimicrobial activity than did R. officinalis oil against E. coli, S. aureus and L. monocytogenes. Complete death time on exposure to Cuminum cyminum L. and Rosmarinus officinalis L. oils were 20 and 25 min 180 and 240 min and 90 and 120 min for E. coli, S. aureus and L. monocytogenes, respectively. Radical-scavenging and antioxidant properties were tested by means of 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay and the β-carotene bleaching test. These properties were compared to those of Thymus x-porlock essential oil, used as a reference ingredient. The radical scavenging performance of the rosemary oil was better than that of C. cyminum. Results from the antioxidant test were better than those provided by the radical-scavenging activity. C. cyminum and R. officinalis essential oils may be considered as potent agents in food preservation.     

Application of response surface methodology and central composite design for the optimisation of supercritical fluid extraction of essential oils from Myrtus communis L. leaves

Essential oils of Myrtus communis L. leaves were obtained using supercritical fluid extraction (SFE) and hydrodistillation methods. The experimental parameters of SFE such as pressure, temperature, modifier volume, static and dynamic extraction time were optimised using a central composite design after a 2ⁿ⁻¹ fractional factorial design. The chemical compositions of the SFE extract were identified by GC–MS and determined by GC–FID. The major components of essential oils obtained by hydrodistillation were α-pinene (31.8%), 1,8-cineole (24.6%), limonene (14.8%), linalool (8.3%) and α-terpinolene (4.8%). However, by using the supercritical carbon dioxide in optimum conditions, only three components represented more than 85% of the extract. Therefore, by using the proper SFE conditions, the supercritical extraction is more selective than the conventional hydrodistillation methods. The oil yields based on the hydrodistillation was 0.47% (v/w). Extraction yields based on the SFE varied in the range of 0.5–6.3% (w/w) under different conditions.     

Essential oil composition of the turpentine tree (Pistacia terebinthus L.) fruits growing wild in Turkey

Constituents of essential oils from fruit samples of the turpentine tree (Pistacia terebinthus L.) collected from fifteen different localities of Turkey on August 2001 were identified by GC–MS. Twenty-eight compounds representing 92.3–100.0% of turpentine fruit oils were identified. The oil yields varied between 0.06% and 0.16%. The highest yield of oil was obtained from fruits of Antalya origin (Akba?-Serik) (0.16%). α-Pinene (51.3%), limonene (39.0%), p-cymen-8-ol (40.0%) and caryophyllene oxide (51.0%) were found as major components for different localities in Turkey. The predominant constituents in most samples were α-pinene (9.5–51.3%), limonene (tr-39.0%) and caryophyllene oxide (tr-51.5). Except for one collection (Manavgat-Antalya), which contained spathulenol (20.7%) and p-cymen-8-ol (40.0%), all the other samples yielded oils rich in α-pinene and limonene. β-Caryophyllene oxide is the most abundant compound in Hisarönü (?zmir), Alanya (Antalya) and Yaylada? (Hatay) oils. Results confirm the effect of locality on the oil content and composition.     

Chemical composition and insecticidal properties of some aromatic herbs essential oils from Algeria

The biological effects on Sitophilus granarius were evaluated for three aromatic herbs essential oils: Foeniculum vulgare, Rosmarius officinalis and Lippia citriodora. Stored grain pests were currently controlled by chemical pesticides. This control method leads to pollution of the environment and intoxication of consumers. Essential oils of aromatic plants are more considered as good control alternative tools. Filter papers treated with 5, 50 and 500 μl of test oil were placed in the bottom cover of 1 l plastic bottle. The insects, 50 adults per bottle, were exposed for 1–5 days. Cumulative mortalities were determined 24 and 120 h after treatment. All treatments were replicated five times. The components of the essential oils were identified through GC and GC–MS. The identity of the constituents was confirmed and their relative proportions determined. The results indicate that these natural products may find potential application as useful, environmentally safe insect control and crop protectant agents.     

Chemical composition,antioxidant and antibacterial activities of the essential oils isolated from Tunisian Thymus capitatus Hoff. et Link.

The chemical composition, antioxidant and antibacterial activities of essential oils isolated by hydrodistillation from the aerial parts of Tunisian Thymus capitatus Hoff. et Link. during the different phases of the plant development, and from different locations, were evaluated. The chemical composition was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The main components of the essential oils were carvacrol (62–83%), p-cymene (5–17%), γ-terpinene (2–14%) and β-caryophyllene (1–4%). The antioxidant activity of the oils (100–1000 mg l⁻¹) was assessed by measurement of metal chelating activity, the reductive potential, the free radical scavenging (DPPH) and by the TBARS assay. The antioxidant activity was compared with that of synthetic antioxidants: butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). Both the essential oils and BHA and BHT showed no metal chelating activity. Although with the other methodologies, there was a general increase in the antioxidant activity, with increasing oil concentration, maxima being obtained in the range of 500 and 1000 mg l⁻¹ for flowering and post-flowering phase oils. Major differences were obtained according to the methodology of antioxidant capacity evaluation. Antibacterial ability of Th. capitatus essential oils was tested by disc agar diffusion against Bacillus cereus, Salmonella sp., Listeria innocua, four different strains of Staphylococus aureus (C15, ATCC25923, CFSA-2) and a multi-resistant form of S. aureus (MRSA-2). Antibacterial properties were compared to synthetic antibiotics. Higher antibacterial activity was observed with the flowering and the post-flowering phase essential oils.     

Composition of peel essential oils from four selected Tunisian Citrus species: Evidence for the genotypic influence

The peel essential oils from four selected Tunisian Citrus species: sweet orange (Citrus sinensis Osbeck), mandarin (Citrus reticulata Blanco); sour orange (Citrus aurantium L.) and pummelo (Citrus grandis Osbeck), cultivated under the same pedoclimatic and cultural conditions have been analysed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). The essential oils content ranged from 1.06% to 4.62% (w/w) in pummelo and mandarin, respectively. The qualitative and quantitative analysis led to the identification of 70 components in all oil samples. The analysed oils consist mainly in monoterpene hydrocarbons (97.59–99.3%), with limonene (92.52–97.3%) and β-pinene (1.37–1.82) being the major constituents. The remaining chemical classes were weakly represented (<1%). Both qualitative and quantitative differences between oil samples have been observed and numerous components have been proposed as marker compounds. Since the influence of different environmental factors has been eliminated, the observed chemical variability between the studied species and cultivars seems likely to results from the genetic variability.     

The in vitro antioxidative properties of the essential oils and methanol extracts of Satureja spicigera (K. Koch.) Boiss. and Satureja cuneifolia ten

This study was designed to examine the in vitro antioxidant activities of the essential oil and methanol extracts of Satureja spicigera and S. cuneifolia from Turkish flora. GC and GC/MS analysis of the essential oils resulted in the identification of 40 and 29 compounds, representing the 99.4% and 99.5% of the oils, respectively. Major constituents of the oils were carvacrol (42.5% and 67.1%), γ-terpinene (21.5% and 15.2%) and p-cymene (20.9% and 6.7%), respectively. Methanol extracts were also obtained from the aerial parts of the plants. The samples were subjected to a screening for their possible antioxidant activities by using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and β-carotene–linoleic acid assays. In general, samples obtained from S. cuneifolia exerted greater antioxidant activities than did those obtained from S. spicigera. In the DPPH test system, free radical-scavenging activity of S. spicigera oil was determined to be 127 ± 1.63 μg/ml, whereas IC₅₀ value of S. cuneifolia was 89.1 ± 2.29 μg/ml. In the β-carotene–linoleic acid test system, antioxidant activities of the oil were 81.7 ± 1.14% and 93.7 ± 1.83%, respectively. Antioxidant activities of the synthetic antioxidant, BHT, ascorbic acid, curcumin and α-tocopherol were also determined in parallel experiments.     

Phytochemical composition and antimicrobial activities of the essential oils from Satureja subspicata Vis. growing in Croatia

The present study describes the phytochemical profile and antimicrobial activity of Satureja subspicata Vis. essential oils, collected in Dalmatia (Croatia). Three samples of essential oils were obtained from the aerial parts of the plant by hydrodistillation and analyzed by GC–MS. From the 24 compounds representing 97.47% of the oils, carvacrol (16.76%), α-pinene (13.58), p-cymene (10.76%), γ-terpinene (9.54%) and thymol methyl ether (8.83%) appear as the main components. The oils also contained smaller percentages of myrcene, linalool, β-caryophyllene, limonene, geranyl acetate, 1-Octen-3-ol, nerol, thymol and borneol. Furthermore, antimicrobial activity of the oil was evaluated using agar diffusion and broth microdilution methods. The antimicrobial test results showed that the oils had a great potential antimicrobial activity against all 13 bacteria and 9 fungal strains. Gram-positive bacteria are more sensitive to the investigated oil, with a range of 0.09 to 6.25 μl/ml than Gram-negative bacteria in the range which is significantly higher from 1.56 to 25.00 μl/ml. Results presented here may suggest that the essential oil of S. subspicata possesses antimicrobial properties, and is therefore a potential source of antimicrobial ingredients for the food and pharmaceutical industry.     

Screening of the antioxidative and antimicrobial properties of the essential oils of Pimpinella anisetum and Pimpinella flabellifolia from Turkey

The aerial parts of two endemic Pimpinella [Pimpinella anisetum Boiss. & Ball. and Pimpinella flabellifolia (Boiss.) Benth. ex Drude] were hydro-distilled to produce oils in the yields of 2.07% (v/w) and 2.61% (v/w), respectively. The oils were analysed by GC and GC/MS. Twenty-one and nineteen components were identified, representing 99.5% and 99.7% of the oils, respectively. The main compounds of P. anisetum were (E)-anethole (82.8%) and methyl chavicol (14.5%), whereas limonene (47.0%), (E)-anethole (37.9%) and α-pinene (6.0%) were the major constituents of P. flabellifolia. The oils were screened for their possible antioxidant activities by two complementary test systems, namely DPPH free radical-scavenging and β-carotene/linoleic acid systems. In the first case, P. anisetum oil exerted greater antioxidant activity than that of P. flabellifolia oil with an IC₅₀ value of 5.62 ± 1.34 μg/ml. In the β-carotene/linoleic acid test system, the oil of P. anisetum was superior to P. flabellifolia with 70.5% ± 2.86 inhibition rate. Essential oils of the plants studied here were also screened for their antimicrobial activities against six bacteria and two fungi. The oils showed moderate antimicrobial activity against all microorganisms tested.     

Chemical composition,antimicrobial, cytotoxic and antioxidant activities of the essential oil of Artemisia indica Willd

Essential oil from the aerial parts of Artemisia indica was analysed by GC-FID and GC–MS. A total of 43 compounds representing 96.8% of the oil were identified and the major components were found to be artemisia ketone (42.1%), germacrene B (8.6%), borneol (6.1%) and cis-chrysanthenyl acetate (4.8%). Antimicrobial activity of the oil was evaluated against seven clinically significant bacterial and two fungal strains. The essential oil and its major constituents exhibited moderate to potent, broad-spectrum antibacterial and antifungal activities targeting both Gram-positive and Gram-negative bacteria. In vitro cytotoxicity evaluation against four human cancer cell lines THP-1 (leukemia), A-549 (lung), HEP-2 (liver) and Caco-2 (colon) showed that the essential oil exhibited concentration dependant growth inhibition in the 10–100 μg/ml dilution range, with IC₅₀ values of 10 μg/ml (THP-1), 25 μg/ml (A-549), 15.5 μg/ml (HEP-2) and 19.5 μg/ml (Caco-2). It was interesting to note that the essential oil also exhibited potent antioxidant activity.     

Variations in essential oil and fatty acid composition during Myrtus communis var. italica fruit maturation

The essential oil and fatty acid composition of Myrtus communis var. italica fruit during its ripening was determined. The effect of the harvesting time on some physical properties of Myrtus fruits, fruit weight and moisture content, were significant. The increase of fruit weight (from 2.54 to 8.79 g% fruits) during ripeness was correlated positively with that of moisture content (from 28% to 72%). Fruit essential oil yields varied from 0.003% to 0.01% and showed a remarkable increase at 60 days after flowering to reach a maximum of 0.11%. Forty-seven volatile compounds were identified in fruit essential oils; 1,8-cineole (7.31–40.99%), geranyl acetate (1.83–20.54%), linalool (0.74–18.92%) and α-pinene (1.24–12.64%) were the main monoterpene compounds. Total fatty acid contents varied from 0.81% to 3.10% during fruit maturation and the predominant fatty acids were linoleic (12.21–71.34%), palmitic (13.58–37.07%) and oleic (6.49–21.89%) acids. The linoleic acid proportions correlated inversely with palmitic and oleic acids during all the stages of ripening.     

Major chemotypes and antioxidative activity of the leaf essential oils of Cinnamomum osmophloeum Kaneh. from a clonal orchard

Essential oils of 92 cutting clones from a clonal orchard of Cinnamomum osmophloeum Kaneh. were obtained by hydrodistillation and characterised by gas chromatography–mass spectrometry. Our results showed that the yields of essential oils ranged between 0.09% and 2.65% (vol/fresh wt). The constituents of essential oils varied among samples. The major chemotypes classified in the individual cutting clones were cinnamaldehyde (50 plants, representing 50–95% of the total volatiles), linalool (1 plant, 73.3%), β-cubebene (2 plants, 59.4% and 78.7%), and cinnamyl acetate (1 plant, 61.8%). The antioxidant activities of the four chemotypes were determined using a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The antioxidant activities of the essential oil decreased in the order of cinnamyl acetate > cinnamaldehyde > β-cubebene > linalool. Indigenous cinnamon oil extract showed a good free radical-scavenging capacity at all concentrations studied, except at 2 μg/ml. The scavenging activity increased with increasing concentration of the extract. The capability of the four essential oil chemotypes to reduce the stable radical, DPPH, to DPPH-H was assayed by a decrease in the IC₅₀ values of 10.4 (cinnamyl acetate type) to 29.7 (linalool type) μg/ml. These results suggest that the leaf essential oil of C. osmophloeum possesses chemical compounds with antioxidant activity which can be used as natural preservatives in food and/or by the pharmaceutical industry. Trees in this plantation which can be used for further propagation for the production of chemotypes of interest were identified.     

The essential oil of Glossogyne tenuifolia

Glossogyne tenuifolia (Labill) Cass. (Compositae) is a traditional anti-pyretic and hepatoprotective herb in The Pescadores Islands. The essential oil of the dried herb, from four seasons, was isolated using a simultaneous steam-distillation and solvent-extraction (SDE) apparatus. The essential oil contents were in the range of 0.48–0.77 mg g⁻¹, with an average of 0.66 mg g⁻¹, and declined with the seasons. Generally, the essential oils from four seasons exhibited similar volatile profiles. A total of 62 different compounds were isolated by the SDE method and, among them, 30 compounds were identified, including 13 terpenes, 16 oxygen-containing compounds (eight alcohols, five aldehydes, one ester and two ketones) and one other compound. Terpenes were predominantly present in the essential oil and accounted for 61.3–76.0% of the essential oil with an average of 69.1%. The second most abundant class was alcohols, accounting for 12.4–15.9% of the essential oil, with an average of 14.1%. Consistently for four seasons, the most abundant eight compounds were in the descending order: p-cymene > β-pinene > β-phellandrene > limonene > cryptone > α-pinene > 4-terpineol + γ-muurolene. However, these eight compounds accounted for 71.5% of the average of the essential oil and, in combination, might give rise to the overall citrus-like aroma of the G. tenuifolia.     

Antioxidant and antiacetylcholinesterase activities of essential oils from Cymbopogon schoenanthus L. Spreng. Determination of chemical composition by GC–mass spectrometry and C NMR

Cymbopogon schoenanthus L. Spreng, is an aromatic herb consumed in salads and used to prepare traditional meat recipes in Tunisia. The chemical composition, antioxidant activities and acetylcholinesterase inhibitory properties of the essential oils from fresh leaves, dried leaves and roots collected from three different locations in southern Tunisia, were evaluated. Essential oils were analysed by GC–mass spectrometry and ¹³C NMR. The major components were limonene (10.5–27.3%), β-phellandrene (8.2–16.3%), δ-terpinene (4.3–21.2%) and α-terpineol (6.8–11.0%). Antioxidant activity was measured by DPPH assay. The results ranged from 36.0% to 73.8% (2 μl of essential oil per mL of test solution).     

Composition of the essential oils from leafy parts of the shoots,flowers and fruits of Eryngium amethystinum from Amiata Mount (Tuscany,Italy)

The essential oils obtained from the leafy parts of the shoots, inflorescences and fruits of Eryngium amethystinum (Apiaceae) from Italy have been studied. The essential oil from the inflorescences was characterised by methyl-derivatives of benzaldehyde (26.4%) and by some phenylpropanoids (3.0%) such as eugenol and (E)-methyl isoeugenol. The essential oil of leafy parts of the shoots showed a higher percentage of sesquiterpenes (31.3%) than monoterpenes (20.2%). The main differences between the two essential oils can be referred to α-pinene and germacrene D: the essential oil of the inflorescences contained much more α-pinene than the other one (25.6% vs. 11.8%), while the contrary is true for germacrene D (14.5% vs. 31.3%).     

Inhibitory effect of Turkish Rosmarinus officinalis L. on acetylcholinesterase and butyrylcholinesterase enzymes

In the current study, we have tested acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activity of the petroleum ether, ethyl acetate, chloroform, and methanol extracts, rosmarinic acid as well as the essential oil obtained from Rosmarinus officinalis L. growing in Turkey by a spectrophotometric method of Ellman using ELISA microplate-reader at 0.2, 0.5, and 1.0 mg/mL concentrations. In addition, quantification of rosmarinic acid, a common phenolic acid found in rosemary, was carried out by reversed-phase HPLC in the methanolic extract of the plant, which was found to have 12.21 ± 0.95% (122.1 ± 9.5 mg/g extract) of rosmarinic acid. Rosmarinic acid was also tested for its AChE and BChE inhibitory effect and found to cause 85.8% of inhibition against AChE at only 1.0 mg/mL. Besides, the essential oil was analyzed by GC–MS technique, which was shown to be dominated by 1,8-cineol (44.42%) and followed by α-pinene (12.57%).     

Variations in the essential oil composition in buds of six blackcurrant (Ribes nigrum L.) cultivars at various development phases

The variations in the content and the composition of dormant bud essential oil in six blackcurrant (Ribes nigrum L.) cultivars collected at various vegetation phases (from December 15, 2004 until April 19, 2005) were studied. Essential oil yield varied from 0.6% to 1.8%, except for the buds harvested in April, when the yield was considerably lower, 0.19–0.27%. Fifty volatile compounds were identified in the bud oils, hydrocarbon (38–55%) and oxygenated (on average 30%) terpenes being the major chemical constituents. Sabinene, δ-3-carene, terpinolene were dominant components, while cis- and trans-β-ocimene, α-thujene, α- and β-pinene, myrcene, α- and β-phellandrene, α- and γ-terpinene, p-cymene, cis- and trans-sabinene hydrate, terpinen-4-ol, α-terpineol, trans-piperitol, bornyl acetate, terpinyl acetate, citronellyl acetate, germacrenes D, β-caryophyllene, α-humulene, α-selinene, δ-cadinene and α-cadinol were found in reasonable amounts. Almiai may be considered as a superior cultivar, as possessing the most even content of oils ant the main constituents at all harvesting periods, except for April; however some other cultivars (Gagatai, Joniniai) accumulated higher amounts of oil at particular vegetation phases. January may be considered as a preferable harvesting time of buds; the amount of major terpenes at this phase was the highest in the all cultivars except for Joniniai. The concentration of the main oil compounds in buds harvested in April was 2–50 times lower than at other periods in the all six cultivars.     

Changes on essential oil composition of coriander (Coriandrum sativum L.) fruits during three stages of maturity

The essential oils composition of coriander (Coriandrum sativum L.) fruits obtained by hydrodistillation was studied at three stages of maturity by GC–FID and GC–MS. Essential oil yields showed marked increase during maturation process and forty one compounds were identified. Geranyl acetate (46.27%), linalool (10.96%), nerol (1.53%) and neral (1.42%) were the main compounds at the first stage of maturity (immature fruits). At the middle stage, linalool (76.33%), cis-dihydrocarvone (3.21%) and geranyl acetate (2.85%) were reported as the main constituents. Essential oils at the final stage of maturity (mature fruits) consist mainly on linalool (87.54%) and cis-dihydrocarvone (2.36%). Additionally, accumulation of monoterpene alcohols and ketones was observed during maturation process of coriander fruit.