Composition and antibacterial activity of the essential oils of four commercial grades of Omani luban, the oleo-gum resin of Boswellia sacra FLUECK

The essential oil compositions of four botanically certified and commercially available samples of Omani lubans (oleo-gum resins of Boswellia sacra Flueck.), locally known as Hoojri, Najdi, Shathari, and Shaabi in Jibali Arabic, obtained from plants growing in four different geographic locations of the Dhofar region of Oman, were analyzed by GC-FID, GC/MS, and (13) C-NMR spectroscopy. The market price of these four grades of lubans differed considerably, according to their color, clump size, and texture. However, this study revealed that Hoojri, the first grade luban, and Shaabi, the fourth grade luban, which greatly differed in their price, closely resembled each other in their essential oil composition, yield, and physicochemical characteristics, except the color and texture. The composition, yield, and specific rotation of the oils of Najdi and Shathari, the second and the third grade lubans, respectively, were different from those of Hoojri and Shaabi, but they both had high limonene contents. Najdi oil was different from the other three oils in terms of its high myrcene content. α-Pinene was the principal component in all the oils and can be considered as a chemotaxonomical marker that confirms the botanical and geographical source of the resins. All the oils showed pronounced activity against a panel of bacteria, and the trend in their bioactivity and their mode of action are discussed.     

Chemical Composition of Juniperus communis L. Cone Essential Oil and Its Variability among Wild Populations in Kosovo

Ripe cones of Juniperus communis L. (Cupressaceae) were collected from five wild populations in Kosovo, with the aim of investigating the chemical composition and natural variation of essential oils between and within wild populations. Ripe cones were collected, air dried, crushed, and the essential oils obtained by hydrodistillation. The essential‐oil constituents were identified by GC‐FID and GC/MS analyses. The yield of essential oil differed depending on the population origins and ranged from 0.4 to 3.8% (v/w, based on the dry weight). In total, 42 compounds were identified in the essential oils of all populations. The principal components of the cone‐essential oils were α‐pinene, followed by β‐myrcene, sabinene, and D ‐limonene. Taking into consideration the yield and chemical composition, the essential oil originating from various collection sites in Kosovo fulfilled the minimum requirements for J. communis essential oils of the European Pharmacopoeia. Hierarchical cluster analysis (HCA) and principal component analysis (PCA) were used to determine the influence of the geographical variations on the essential‐oil composition. These statistical analyses suggested that the clustering of populations was not related to their geographic location, but rather appeared to be linked to local selective forces acting on the chemotype diversity.     

Seasonal and Geographical Influences on the Chemical Composition of Juniperus phoenicea L. Essential Oil Leaves from the Northern Tunisia

The essential‐oil composition of 60 individual trees of Juniperus phoenicea L. from four Tunisian populations in three different periods were investigated by GC and GC/MS analyses. 59 Compounds were identified in the oils, and a relatively high variation in their contents was found. All the oils were dominated by the terpenic hydrocarbon fraction, and the main component was α‐pinene (20.28–40.86%). The results of the oil compositions were processed by hierarchical clustering and principal component analysis (PCA) allowing establishing four groups of essential‐oils differentiated by one compound or more. Pattern of geographic variation in essential‐oil composition indicated that individuals from the continental site (Makthar) were clearly distinguished from those from littoral localities (Tabarka, Hawaria, and Rimel).     

Composition and Antimicrobial Activity of the Essential Oils of Laserpitium latifolium L. and L. ochridanum Micevski (Apiaceae)

The chemical composition and antimicrobial activity of essential oils of Laserpitium latifolium and L. ochridanum were investigated. The essential oils were isolated by steam distillation and characterized by GC‐FID and GC/MS analyses. All essential oils were distinguished by high contents of monoterpenes, and α‐pinene was the most abundant compound in the essential oils of L. latifolium underground parts and fruits (contents of 44.4 and 44.0%, resp.). The fruit essential oil was also rich in sabinene (26.8%). Regarding the L. ochridanum essential oils, the main constituents were limonene in the fruit oil (57.7%) and sabinene in the herb oil (25.9%). The antimicrobial activity of these essential oils as well as that of L. ochridanum underground parts, whose composition was reported previously, was tested by the broth‐microdilution method against four Gram‐positive and three Gram‐negative bacteria and two Candida albicans strains. Except the L. latifolium underground‐parts essential oil, the other investigated oils showed a high antimicrobial potential against Staphylococcus aureus, S. epidermidis, Micrococcus luteus, or Candida albicans (minimal inhibitory concentrations of 13.0–73.0 μg/ml), comparable to or even higher than that of thymol, which was used as reference compound.     

Chemical constituents and antimicrobial activity of the leaf and rhizome oils of Alpinia pahangensis Ridl., an endemic wild ginger from peninsular Malaysia

The essential oils from the leaves and rhizomes of Alpinia pahangensis Ridl ., collected from Pahang, Peninsular Malaysia, were obtained by hydrodistillation, and their chemical compositions were determined by GC and GC/MS analyses. The major components of the rhizome oil were γ‐selinene (11.60%), β‐pinene (10.87%), (E,E)‐farnesyl acetate (8.65%), and α‐terpineol (6.38%), while those of the leaf oil were β‐pinene (39.61%), α‐pinene (7.55%), and limonene (4.89%). The investigation of the antimicrobial activity of the essential oils using the broth microdilution technique revealed that the rhizome oil of A. pahangensis inhibited five Staphylococcus aureus strains with minimum inhibitory concentration (MIC) values between 0.08 and 0.31 μg/μl, and four selected fungi with MIC values between 1.25 and 2.50 μg/μl.     

Chemical Composition of the Essential Oils from Different Morphological Parts of Pinus cembra L.

The essential oils from needles, twigs, bark, wood, and cones of Pinus cembra were analyzed by GC‐FID, GC/MS, and ¹H‐NMR spectroscopy. More than 130 compounds were identified. The oils differed in the quantitative composition. The principal components of the oil from twigs with needles were α‐pinene (36.3%), limonene (22.7%) and β‐phellandrene (12.0%). The needle oil was dominated by α‐pinene (48.4%), whereas in the oil from bark and in the oil from twigs without needles there were limonene (36.2% and 33.6%, resp.) and β‐phellandrene (18.8% and 17.1%, resp.). The main constituents of the wood oil as well as cone oil were α‐pinene (35.2% and 39.0%, resp.) and β‐pinene (10.4% and 18.9%, resp.). The wood oil and the cone oil contained large amounts of oxygenated diterpenes in comparison with needle, twig, and bark oils.     

Comparison of Chemical Composition of the Essential Oils from Different Botanical Organs of Pinus mugo Growing in Poland

The essential oils from needles, twigs, bark, wood, cones and young shoots of Pinus mugo were analyzed by GC, GC/MS, and ¹H‐NMR spectroscopy. More than 130 compounds were identified. The oils differed in the quantitative composition. The principal components of the oil from twigs with needles were 3‐carene (23.8 %), myrcene (22.3 %), and α‐pinene (10.3 %). The needle oil contained mainly α‐pinene (18.6 %), 3‐carene (11.3 %), and bornyl acetate (8.3 %). The oils from twigs without needles, young shoots, bark, and wood were dominated by 3‐carene (28.6 %, 15.0 %, 18.5 %, and 34.6 %, respectively) and myrcene (23.4 %, 24.0 %, 24.6 %, and 9.4 %, respectively). In the cone oil (E)‐β‐caryophyllene was the main constituent (24.0 %).     

Composition and Antiviral Activity of the Essential Oils of Eryngium alpinum and E. amethystinum

The chemical compositions of the essential oils obtained by hydrodistillation of the aerial parts of Croatian Eryngium alpinum L. and E. amethystinum L. were characterized by GC‐FID and GC/MS analyses. The main components identified were the sesquiterpene β‐caryophyllene (19.7%) in the oil of E. amethystinum and the oxygenated sesquiterpene caryophyllene oxide (21.6%) in the oil of E. alpinum. Overall, 32 and 35 constituents were detected in the essential oils of the aerial parts of E. alpinum and E. amethystinum, respectively, representing 92.4 and 93.1% of the total oil compositions. The essential oils of both Eryngium species were proved to reduce the number of lesions in the local host Chenopodium quinoa infected with cucumber mosaic virus and an associated satellite. This is the first investigation of antiphytoviral activity of essential oils of Eryngium species.     

Chemical Composition and Antimicrobial Activity of Essential Oils from Scabiosa arenaria Forssk. Growing Wild in Tunisia

The essential oils isolated from three organs, i.e., fruits, stems and leaves, and flowers, of the endemic North African plant Scabiosa arenaria Forssk . were screened for their chemical composition, as well as their possible antibacterial, anticandidal, and antifungal properties. According to the GC‐FID and GC/MS analyses, 61 (99.26% of the total oil composition), 79 (98.43%), and 51 compounds (99.9%) were identified in the three oils, respectively. While α‐thujone (34.39%), camphor (17.48%), and β‐thujone (15.29%) constituted the major compounds of the fruit oil, chrysanthenone (23.43%), together with camphor (12.98%) and α‐thujone (10.7%), were the main constituents of the stem and leaf oil. In the case of the flower oil, also chrysanthenone (38.52%), camphor (11.75%), and α‐thujone (9.5%) were identified as the major compounds. Furthermore, the isolated oils were tested against 16 Gram‐positive and Gram‐negative bacteria, four Candida species, and nine phytopathogenic fungal strains. It was found that the oils exhibited interesting antibacterial and anticandidal activities, comparable to those of thymol, which was used as positive control, but no activity against the phytopathogenic fungal strains was observed.     

Comprehensive two‐dimensional gas chromatography–mass spectrometry analysis of volatile constituents in Thai vetiver root oils obtained by using different extraction methods

Introduction – Vetiver root oil is known as one of the finest fixatives used in perfumery. This highly complex oil contains more than 200 components, which are mainly sesquiterpene hydrocarbons and their oxygenated derivatives. Since conventional GC‐MS has limitation in terms of separation efficiency, the comprehensive two‐dimensional GC‐MS (GC × GC‐MS) was proposed in this study as an alternative technique for the analysis of vetiver oil constituents. Objective – To evaluate efficiency of the hyphenated GC × GC‐MS technique in terms of separation power and sensitivity prior to identification and quantitation of the volatile constituents in a variety of vetiver root oil samples. Methodology – Dried roots of Vetiveria zizanioides were subjected to extraction using various conditions of four different methods; simultaneous steam distillation, supercritical fluid, microwave‐assisted, and Soxhlet extraction. Volatile components in all vetiver root oil samples were separated and identified by GC‐MS and GC × GC‐MS. The relative contents of volatile constituents in each vetiver oil sample were calculated using the peak volume normalization method. Results – Different techniques of extraction had diverse effects on yield, physical and chemical properties of the vetiver root oils obtained. Overall, 64 volatile constituents were identified by GC‐MS. Among the 245 well‐resolved individual components obtained by GC × GC‐MS, the additional identification of 43 more volatiles was achieved. Conclusion – In comparison with GC‐MS, GC × GC‐MS showed greater ability to differentiate the quality of essential oils obtained from diverse extraction conditions in terms of their volatile compositions and contents. Copyright © 2009 John Wiley & Sons, Ltd.     

Comparison of the Composition and Antimicrobial Activities of the Essential Oils of Green Branches and Leaves of Egyptian Navel Orange (Citrus sinensis (L.) Osbeck var. malesy)

The essential oils isolated from the leaves and green branches of the Egyptian navel orange trees were analyzed by GC and GC/MS. A total of 33 and 24 compounds were identified from the oils of the leaves and branches accounting for 96.0% and 97.9%, respectively, of the total detected constituents. The major ones were sabinene (36.5; 33.0%), terpinen‐4‐ol (8.2; 6.2%), δ‐3‐carene (7.0; 9.4%), limonene (6.8; 18.7%), trans‐ocimene (6.7; 6.1%), and β‐myrcene (4.5; 4.4%). The antimicrobial activities of both oils were evaluated using the agar‐well diffusion method toward three representatives for each of Gram‐positive bacteria, Gram‐negative bacteria, and fungi. The oil of leaves was more effective as antimicrobial agent than that of the branches. Streptococcus pyogenes, Staphylococcus aureus, Salmonella typhimurium, and Aspergillus fumigatus were the most sensitive bacteria and fungi by the leaves oil.     

Larvicidal and Nematicidal Activities of the Leaf Essential Oil of Croton regelianus

The chemical composition of the leaf essential oil of Croton regelianus collected from wild plants growing in two different sites at Ceará State (Brazil) was analyzed by GC/MS and GC‐FID. Twenty monoterpenoids, representing more than 96% of the chemical composition of the oils, were identified and quantified. The oils showed similar chemical composition but considerable variation in the levels of each constituent. Ascaridole (33.9–17.0%), p‐cymene (22.3–21.6%), and camphor (13.0–3.1%) were the predominant constituents. The monoterpene ascaridole was isolated and characterized by spectroscopic data. The essential oils and the isolated compounds were tested against Aedes aegypti and Artemia sp. larvae, and the root knot nematode Meloidogyne incognita. The bioassay results show that the essential oil of C. regelianus and ascaridole were moderately active against the M. incognita, but strongly effective against both A. aegypti and Artemia sp. larvae.     

Variation of the Chemical Composition and Antimicrobial Activity of the Essential Oils of Natural Populations of Tunisian Daucus carota L. (Apiaceae)

The essential oils of Daucus carota L. (Apiaceae) seeds sampled from ten wild populations spread over northern Tunisia were characterized by GC‐FID and GC/MS analyses. In total, 36 compounds were identified in the D. carota seed essential oils, with a predominance of sesquiterpene hydrocarbons in most samples (22.63–89.93% of the total oil composition). The main volatile compounds identified were β‐bisabolene (mean content of 39.33%), sabinene (8.53%), geranyl acetate (7.12%), and elemicin (6.26%). The volatile composition varied significantly across the populations, even for oils of populations harvested in similar areas. The chemometric principal component analysis and the hierarchical clustering identified four groups, each corresponding to a composition‐specific chemotype. The in vitro antimicrobial activity of the isolated essential oils was preliminarily evaluated, using the disk‐diffusion method, against one Gram‐positive (Staphylococcus aureus) and two Gram‐negative bacteria (Escherichia coli and Salmonella typhimurium), as well as against a pathogenic yeast (Candida albicans). All tested essential oils exhibited interesting antibacterial and antifungal activities against the assayed microorganisms.     

Bark Essential Oil of Cedrelopsis grevei from Madagascar: Investigation of Steam‐Distillation Conditions

The effect of the distillation time on the yield and chemical composition of the bark essential oil of Cedrelopsis grevei Baill. was investigated. Distillation kinetics were determined for three batches of bark sampled from two sites, i.e., Itampolo (batches IT1 and IT2) and Salary (SAL), located in a region in the south of Madagascar with characteristically large populations of C. grevei. The bark samples were subjected to steam distillation, and the essential oil was collected at 3‐h intervals. The total yield (calculated after 14 h of distillation) varied from 0.9 to 1.7%, according to the batch tested. Moreover, the essential oils obtained were characterized by GC‐FID and GC/MS analyses. During the course of the distillation, the relative percentages of the most volatile components (monoterpenes and sesquiterpene hydrocarbons) diminished progressively, whereas the least volatile ones (oxygenated derivatives) increased at a consistent rate. Principal component analysis (PCA) and agglomerative hierarchical clustering analysis (AHC) of the results, performed on 13 principal components, allowed distinguishing three chemical groups, corresponding to the three batches, irrespective of the distillation time. This indicated that the chemical variability currently observed with commercial samples is not mainly linked to the experimental conditions of the extraction process, as the distillation time did not significantly alter the chemical composition of the essential oils.     

Comparative Chemical Composition of the Essential Oils Obtained by Microwave‐Assisted Hydrodistillation and Hydrodistillation from Agrimonia pilosa Ledeb. Collected in Three Different Regions of China

Conventional hydrodistillation (HD) and microwave‐assisted hydrodistillation (MAHD) were performed to obtain the volatile oils of Agrimonia pilosa Ledeb . harvested in three different regions of China, which were subsequently characterized by GC‐FID and GC/MS analyses. Compared with HD, MAHD was advantageous in terms of energy savings and extraction time (60 vs. 240 min for MAHD and HD, resp.). The chemical composition varied among the different oils obtained, and the variations in the contents of the main constituents of the oils were irregular. Hence, these variations affected both the quantity and composition of the oils. The oil yields (0.15–0.21%) were affected by the method of extraction and the region of harvest, with the maximum amount of oil obtained by MAHD for the plants collected in Hubei (HB) and the minimum yield obtained by HD for the plants from Zhejing (ZJ). Hexadecanoic acid constituted the major compound of the essential oils, with the highest content found in the oil obtained by HD for plants from HB (41.18%) and the lowest one found in the oil obtained by MAHD from plants from ZJ (11.83%). Microwave irradiation did not adversely affect the composition of the essential oils. The findings show that MAHD is a modern, green, and fast technology.     

Phytochemical Diversity of Murraya koenigii (L.) Spreng. from Western Himalaya

Murraya koenigii (L.) Spreng. (Rutaceae), commonly known as ‘curry leaf tree’, is a popular spice and condiment of India. To explore the diversity of the essential‐oil yield and aroma profile of curry leaf, growing wild in foot and mid hills of north India, 58 populations were collected during spring season. M. koenigii populations were found to grow up to an altitude of 1487 m in north India. Comparative results showed considerable variations in the essential‐oil yield and composition. The essential‐oil yield varied from 0.14 to 0.80% in shade‐dried leaves of different populations of M. koenigii. Analysis of the essential oils by GC and GC/MS, and the subsequent classification by statistical analysis resulted in four clusters with significant variations in their terpenoid composition. Major components of the essential oils of investigated populations were α‐pinene ( 2 ; 4.5–71.5%), sabinene ( 3 ; <0.05–66.1%), (E)‐caryophyllene ( 11 ; 1.6–18.0%), β‐pinene ( 4 ; <0.05–13.6%), terpinen‐4‐ol ( 9 ; 0.0–8.4%), γ‐terpinene ( 8 ; 0.2–7.4%), limonene ( 7 ; 1.1–5.5%), α‐terpinene ( 6 ; 0.0–4.5%), (E)‐nerolidol ( 14 ; 0.0–4.1%), α‐humulene ( 12 ; 0.6–3.5%), α‐thujene ( 1 ; 0.0–2.5%), β‐elemene ( 10 ; 0.2–2.4%), β‐selinene ( 13 ; 0.2–2.3%), and myrcene ( 5 ; 0.5–2.1%). Comparison of the present results with those in earlier reports revealed new chemotypes of M. koenigii in investigated populations from Western Himalaya. The present study documents M. koenigii populations having higher amounts of sabinene ( 3 ; up to 66.1%) for the first time.     

Chemical Composition and Allelopathic Potential of Essential Oils Obtained from Acacia cyanophylla Lindl. Cultivated in Tunisia

Acacia cyanophylla Lindl . (Fabaceae), synonym Acacia saligna (Labill .) H. L.Wendl ., native to West Australia and naturalized in North Africa and South Europe, was introduced in Tunisia for rangeland rehabilitation, particularly in the semiarid zones. In addition, this evergreen tree represents a potential forage resource, particularly during periods of drought. A. cyanophylla is abundant in Tunisia and some other Mediterranean countries. The chemical composition of the essential oils obtained by hydrodistillation from different plant parts, viz., roots, stems, phyllodes, flowers, and pods (fully mature fruits without seeds), was characterized for the first time here. According to GC‐FID and GC/MS analyses, the principal compound in the phyllode and flower oils was dodecanoic acid ( 4 ), representing 22.8 and 66.5% of the total oil, respectively. Phenylethyl salicylate ( 8 ; 34.9%), heptyl valerate ( 3 ; 17.3%), and nonadecane (36%) were the main compounds in the root, stem, and pod oils, respectively. The phyllode and flower oils were very similar, containing almost the same compounds. Nevertheless, the phyllode oil differed from the flower oil for its higher contents of hexahydrofarnesyl acetone ( 6 ), linalool ( 1 ), pentadecanal, α‐terpineol, and benzyl benzoate ( 5 ) and its lower content of 4 . Principal component and hierarchical cluster analyses separated the five essential oils into four groups, each characterized by its main constituents. Furthermore, the allelopathic activity of each oil was evaluated using lettuce (Lactuca sativa L.) as a plant model. The phyllode, flower, and pod oils exhibited a strong allelopathic activity against lettuce.     

Chemical Composition and Antibacterial Activity of Essential Oils from Different Parts of Litsea cubeba

The composition of the essential oils obtained by hydrodistillation of different parts of Litsea cubeba, including roots, stems, leaves, alabastra (flower buds), flowers, and fruits, were investigated by GC (RI) and GC/MS. The antimicrobial activity of the oils was assessed with disc diffusion and microbroth dilution assays. The results showed large variations in the composition among the different oils. The major components in the oils from roots and fruits, from stems, leaves, and alabastra, and from flowers were citral B (neral), β‐phellandrene, and β‐terpinene, respectively. The inhibition zone (DD) and MIC values for the bacterial strains tested, which were all sensitive to the essential oil of L. cubeba, were in the range of 10.1–35.0 mm and 100–1000 μg/ml, respectively. Hence, the oils of the various parts showed moderate activity against the tested bacteria. This investigation showed that the antibacterial activity of L. cubeba was attributed to the essential oils, thus they can be a potential medicinal resource.     

Chemical Composition and Antifungal Activity of the Essential Oils of Lavandula pedunculata (Miller) Cav.

The chemical composition and antifungal activity of the essential oils of Lavandula pedunculata (Miller ) Cav. , harvested in North and Central Portugal, were investigated. The essential oils were isolated by hydrodistillation and analyzed by GC and GC/MS. The minimal‐inhibitory concentration (MIC) and the minimal‐lethal concentration (MLC) of the essential oils and of their major constituents were used to evaluate the antifungal activity against different strains of fungi involved in candidosis, dematophytosis, and aspergillosis. The oils were characterized by a high percentage of oxygenated monoterpenes, the main compounds being 1,8‐cineole (2.4–55.5%), fenchone (1.3–59.7%), and camphor (3.6–48.0%). Statistical analysis differentiated the essential oils into two main types, one characterized by the predominance of fenchone and the other one by the predominance of 1,8‐cineole. Within the 1,8‐cineole chemotype, two subgroups were well‐defined taking into account the percentages of camphor. A significant antifungal activity of the oils was found against dermatophyte strains. The essential oil with the highest content of camphor was the most active with MIC and MLC values ranging from 0.32–0.64 μl/ml.     

Chemical Variability,Antioxidant and Antifungal Activities of Essential Oils and Hydrosol Extract of Calendula arvensis L. from Western Algeria

The chemical composition of the essential oils and hydrosol extract from aerial parts of Calendula arvensis L. was investigated using GC‐FID and GC/MS. Intra‐species variations of the chemical compositions of essential oils from 18 Algerian sample locations were investigated using statistical analysis. Chemical analysis allowed the identification of 53 compounds amounting to 92.3 – 98.5% with yields varied of 0.09 – 0.36% and the main compounds were zingiberenol 1 (8.7 – 29.8%), eremoligenol (4.2 – 12.5%), β‐curcumene (2.1 – 12.5%), zingiberenol 2 (4.6 – 19.8%) and (E,Z)‐farnesol (3.5 – 23.4%). The study of the chemical variability of essential oils allowed the discrimination of two main clusters confirming that there is a relation between the essential oil compositions and the harvest locations. Different concentrations of essential oil and hydrosol extract were prepared and their antioxidant activity were assessed using three methods (2,2‐diphenyl‐1‐picrylhydrazyl, Ferric‐Reducing Antioxidant Power Assay and β‐carotene). The results showed that hydrosol extract presented an interesting antioxidant activity. The in vitro antifungal activity of hydrosol extract produced the best antifungal inhibition against Penicillium expansum and Aspergillus niger, while, essential oil was inhibitory at relatively higher concentrations. Results showed that the treatments of pear fruits with essential oil and hydrosol extract presented a very interesting protective activity on disease severity of pears caused by P. expansum.