Volatile constituents of the fruit and leaf oils of Thuja orientalis L. grown in Iran

The composition of the hydrodistilled essential oils from the fruits and leaves of Thuja orientalis L. grown in Iran was analyzed by GC/MS. Nineteen and twenty-eight compounds have been identified in the volatile oils of the fruit and leaf, respectively. While the fruit oil contained alpha-pinene (52.4%), delta-3-carene (14.2%), alpha-cedrol (6.5%) and beta-phellandrene (5.1%), the leaf oil contained alpha-pinene (21.9%), alpha-cedrol (20.3%), delta-3-carene (10.5%) and limonen (7.2%) as the main components.     

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.     

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 of essential oils of four Eucalyptus species and their phytotoxicity on silverleaf nightshade (Solanum elaeagnifolium Cav.) in Australia

Phytotoxicity and chemical composition of essential oils from four selected Eucalyptus species in Australia were investigated. Essential oils had stronger inhibitory effects on germination and seedling growth of silverleaf nightshade (Solanum elaeagnifolium Cav.) when compared with a commercial eucalyptus oil and with 1,8-cineole. E. salubris oil had the highest inhibition index for silverleaf nightshade germination, root growth and shoot growth, while E. spathulata had the lowest inhibitory effect except root growth. Gas chromatography-mass spectrometry analysis revealed 56 compounds present in E. salubris oil, with 1,8-cineole (57.6?%), ??-pinene (10.9?%) and p-cymene (8.3?%) predominant. E. dundasii oil contained 55 identified compounds with 1,8-cineole (65.5?%) and ??-pinene (19.9?%) being the richest fractions. There were 56 compounds identified from E. brockwayii oil with ??-pinene (31.1?%), isopentyl isovalerate (20.2?%) and 1,8-cineole (16.9?%) as the most abundant components. E. spathulata oil contained 60 compounds, predominantly 1,8-cineole (52.9?%) and ??-pinene (31.0?%). Further study is required to determine the phytoxicity of the individual identified compounds on silverleaf nightshade and whether the observed phytotoxicity is attributable to a single compound or to the synergistic effects of several compounds.     

Chemical Composition and Antimicrobial and Allelopathic Activity of Tunisian Conyza sumatrensis (Retz.) E.Walker Essential Oils

Conyza sumatrensis (Retz.) E.Walker (Asteraceae) is a spontaneous annual herb, fairly widespread throughout Tunisia, which has rarely been studied or valued in any sector. Essential oils were obtained by hydrodistillation of different parts (flower heads, leaves, stems, and roots) of C. sumatrensis plants, which were collected in autumn (November 2007) at the flowering stage in the area of Monastir, Tunisia. In total, 98 compounds, representing 88.1–99.3% of the oil composition, were identified by GC‐FID and GC/MS analyses. The root essential oil was distinguished by its high content in acetylenes (matricaria ester, 4 ; 74.3%), while those from flower heads and leaves were dominated by oxygenated sesquiterpenes (61.1 and 50.3%, resp.). The oils of C. sumatrensis from Tunisia belonged to a matricaria ester/caryophyllene oxide chemotype. All the oils were evaluated for antibacterial, antifungal, and allelopathic activities. The results indicate that the leaf oil exhibited significant in vitro antibacterial activity against Enterococcus faecalis, Staphylococcus aureus, and Proteus mirabilis and that the C. sumatrensis oils isolated from the aerial parts presented high mycelia‐growth inhibition of Candida albicans and the filamentous fungi tested. Moreover, the essential oils of the different plant parts inhibited the shoot and root growth of Raphanus sativus (radish) seedlings. Indeed, the inhibition of the hypocotyl growth varied from 28.6 to 90.1% and that of the radicle from 42.3 to 96.2%.     

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.     

不同生长年限巨尾桉叶挥发性成分GC-MS分析

为了分析不同年限巨尾桉叶挥发油的化学成分及生长年限对化学成分组成的影响,采用水蒸气蒸馏法,分别提取2006～2010年种植的巨尾桉叶片中的挥发性成分,并用气相色谱质谱联用技术分析鉴定其化学成分。结果表明:不同生长年限的巨尾桉叶片挥发油产量在0.55%～1.35%之间,随生长年限的增加而升高。利用GC-MS共鉴定出63个化合物,占总挥发油的93.00%～97.07%。其中相对含量较高的物质为:1,8-桉叶油素(55.72%～63.47%)、α-松油醇(9.78%～14.15%)、乙酸松油酯(4.96%～7.06%)、α-蒎烯(0.99%～4.31%)、龙脑(2.40%～4.89%)。由于生长年限的不同,挥发油中物质的组成及相对含量均存在差异。     

Antibacterial activity of the essential oil from Rosmarinus officinalis and its major components against oral pathogens

The essential oil of Rosmarinus officinalis L. (rosemary) was obtained by hydro-distillation and analysed by gas chromatography-mass spectrometry. Sixty-two constituents were identified, representing 98.06% of the total oil content. Oxygenated monoterpenes were the predominant components. The rosemary oil was characterized as having prominent (> 5%) contents of camphor (18.9%), verbenone (11.3%), a-pinene (9.6%), beta-myrcene (8.6%), 1,8-cineole (8.0%), and beta-caryophyllene (5.1%). The antimicrobial activity of the oil as well as of its major constituents was tested against the following microorganisms: Streptococcus mutans, Streptococcus mitis, Streptococcus sanguinis, Streptococcus salivarius, Streptococcus sobrinus, and Enterococcus faecalis, which are potentially responsible for the formation of dental caries in humans. The microdilution method was used for determination of the minimum inhibitory concentration (MIC) during evaluation of the antibacterial activity. The essential oil displayed low activity against the selected microorganisms. In the present study, the pure major compounds were more active than the essential oil. Among all the microorganisms tested, the pathogen S. mitis was the most susceptible and E. faecalis was the most resistant to the evaluated samples. This is the first report on antimicrobial activity of the major components of rosemary oil against oral pathogens.     

栽培地区、采收季节和株龄对迷迭香精油成分和抑菌活性的影响

采用气相色谱-质谱联用的方法,研究了不同提取部位、栽培地区、采收季节和株龄对迷迭香精油提取率、成分和抑菌活性的影响。结果表明,在贵州栽培的迷迭香叶子中精油的主要成分为α-蒎烯（31.88%–39.09%）、1,8-桉叶素（8.82%–10.97%）和樟脑（7.63%–11.59%）;茎中精油的主要成分为龙脑（26.62%–39.05%）、樟脑（11.41%–15.27%）和α-蒎烯（7.23%–17.80%）;茎中精油的抑菌活性强于叶中精油。北京地区栽培的迷迭香,其叶子中精油的主要成分为樟脑（27.92%）和L-β-蒎烯（25.28%）,抑菌活性强;茎中精油和贵州栽培的成分和活性均相似。对于采收季节,夏季采收的迷迭香精油提取率高,抑菌活性强。而株龄对精油的成分和抑菌活性影响不大。该研究为我国引种迷迭香的合理配置栽培、采收、生产条件和高效开发利用其抑菌活性提供了科学的依据。     

A comparative study of Scalesia species (Asteraceae) by gas chromatographic analysis of the monoterpene hydrocarbons of their essential oils

ADSERSEN, A. & SVENDSEN, A. B., 1986. A comparative study of Scalesia species (Asteraceae) by gas chromatographic analysis of the monoterpene hydrocarbons of their essential oils. The monoterpene hydrocarbons of the essential oils of 13 species of Scalesia , Asteraceae, endemic to the Galapagos Islands, were analysed by gas chromatography to determine whether the composition of these compounds could show any characteristics for the various species. Marked differences in the monoterpene hydrocarbon patterns of the Scalesia species investigated were observed. Whereas a-pinene was usually found in amounts of 30–50%, Scalesia villosa contained only 12%. Sabinene usually occurred in amounts of 10-1.5%, but S. divisa and S. affinis contained about twice as much. The limonene content was usually less than 1%, but S. microcephala, S. baurii and S. affinis contained amounts varying from about 2% to 9.5%.     

Antifungal activity of the essential oils from some species of the genus Pinus

The chemical composition of the essential oils from the needles of Pinus ponderosa (north american pine), P. resinosa (red pine) and P. strobus (eastern white pine) has been determined by GC/MS (FID). The essential oils from P. resinosa and P. ponderosa in comparison to P. strobus have been characterized by the higher content of beta-pinene (42.4%, 45.7% and 7.9% respectively). On the other hand, a-pinene (17.7%) and germacrene D (12.2%) were dominant compounds of P strobus. Moreover the essential oil from P. resinosa was more rich in myrcene-15.9%. Estragole and delta-3-carene, each one in amount ca 8% were identified only in P. ponderosa. The content of essential oils in the needles slightly varied--0.65%--P. resinosa, 0.4%--P strobus, 0.3%--P. ponderosa. The antifungal activity has been investigated towards Fusarium culmorum, F solani and F. poae. The strongest activity was observed for the essential oil from P. ponderosa, which fully inhibited the growth of fungi at the following concentrations--F. culmorum, F. solani at 2% and F. poae at 5%.     

Antimicrobial,antibiofilm and antitumor activities of essential oil of Agastache rugosa from Xinjiang,China

In the study, we evaluated chemical composition and antimicrobial, antibiofilm, and antitumor activities of essential oils from dried leaf essential oil of leaf and flower of Agastache rugosa for the first time. Essential oil of leaf and flower was evaluated with GC and GC–MS methods, and the essential oil of flower revealed the presence of 21 components, whose major compounds were pulegone (34.1%), estragole (29.5%), and p-Menthan-3-one (19.2%). 26 components from essential oil of leaf were identified, the major compounds were p-Menthan-3-one (48.8%) and estragole (20.8%). At the same time, essential oil of leaf, there is a very effective antimicrobial activity with MIC ranging from 9.4 to 42 μg ml⁻¹ and potential antibiofilm, antitumor activities for essential oils of flower and leaf essential oil of leaf. The study highlighted the diversity in two different parts of A. rugosa grown in Xinjiang region and other places, which have different active constituents. Our results showed that this native plant may be a good candidate for further biological and pharmacological investigations.     

Chemical Composition and In Vitro Cytotoxicity of Essential Oils from Leaves and Flowers of Callistemon citrinus from Western Himalayas

Background

Plant-based traditional system of medicine continues to play an important role in healthcare. In order to find new potent source of bioactive molecules, we studied the cytotoxic activity of the essential oils from the flowers and leaves of Callistemon citrinus. This is the first report on anticancer potential of essential oils of C. citrinus.

Methods

Cytotoxicity of essential oil was evaluated using sulfo-rhodamine B (SRB) assay against human lung carcinoma (A549), rat glioma (C-6), human colon cancer (Colo-205) and human cervical cancer (SiHa) cells. Apoptosis induction was evaluated by caspase-3/7 activity which was further confirmed by western blotting. Percentage cell apoptosis was determined by Annexin V based dead cell assay followed by DNA content as cell cycle analysis against A549 and C-6 cells. While 3-(4,5-dimethythiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay was used to check the toxicity against normal human peripheral blood mononuclear cells (PBMCs), the immunomodulatory activity on mouse splenocytes was evaluated using SRB assay.

Results

The GC and GC-MS analysis of these essential oils revealed high content of α-pinene (32.3%), limonene (13.1%) and α-terpineol (14.6%) in leaf sample, whereas the flower oil was dominated by 1,8-cineole (36.6%) followed by α-pinene (29.7%). The leaf oil contained higher amount of monoterpene hydrocarbons (52.1%) and sesquiterpenoids (14%) as compared to flower oil (44.6% and 1.2%, respectively). However, the flower oil was predominant in oxygenated monoterpenes (43.5%). Although both leaf and flower oils showed highest cytotoxicity on A549 cells (61.4%±5.0 and 66.7%±2.2, respectively), only 100 μg/mL flower oil was significantly active against C-6 cells (69.1%±3.1). Interestingly, no toxicity was recorded on normal cells.

Conclusion

Higher concentration of 1,8-cineole and/or synergistic effect of the overall composition were probably responsible for the efficacy of flower and leaf oils against the tested cells. These oils may form potential source of natural anti-cancer compounds and play important role in human health.     

广西产生姜精油成分的研究

采用水蒸汽蒸馏法,提取三种广西产生姜的精油,并进行了分析比较。通过GC/MS/DS技术对姜的精油进行定性、定量分析,检出53个成分,鉴定其中34个,占精油的92.2%。     

Canola,corn, and vegetable oils as alternatives for wheat germ oil in fruit fly larval diets

Four wheat germ oil alternatives (corn oil, vegetable oil, canola oil with 10% vitamin E, and canola oil with 20% vitamin E), purchased from a local supermarket in Hawaii, were added to a fruit fly liquid larval diet as a replacement for wheat germ oil in the rearing of fruit fly larvae. The oils were tested on three species of fruit flies in Hawaii, Ceratitis capitata (TSL strain), Bactrocera dorsalis, and Bactrocera cucurbitae. They were evaluated for their efficacy in replacing WGO, based on: pupal recovery (%), larval duration (d), pupal weight (mg), adult emergence (%), adult fliers (%), mating (%), egg production per female per day, egg hatch (%), and peak egging period (d). Diets with WGO and without any oil were used as controls. The objective of the study was to select the most cost effective alternative oils with the best performance to replace the currently used WGO, which is pricey and hard to find. The results showed that there was no significant difference in performance among the tested oils in B. cucurbitae and B. dorsalis as regards the above mentioned parameters. Lower mating rate was observed in B. cucurbitae from those reared in vegetable oil and canola oil (10% vitamin E) diet. Lower egg production and egg hatch were obtained with B. dorsalis whose larvae were reared in vegetable and canola oil (both 10% and 20% vitamin E). Vegetable oil diet seemed to reduce pupal weight, shorten larval duration, and increase pupal recovery of C. capitata. The results suggest that WGO can be substituted with corn oil, vegetable oil, or canola oils for B. cucurbitae, while corn oil is a better alternative for B. dorsalis, and vegetable oil is best for C. capitata.     

Effect of Growth Stage on Essential‐Oil Yield and Composition of Daucus sahariensis

The essential oils obtained by hydrodistillation from Daucus sahariensis Murb . harvested at three different growth stages were characterized by GC/MS analysis. In total, 88 compounds were identified, with myristicin (29.8–51.7%), myrcene (6.7–31.1%), α‐pinene (11.6–14.8%), and limonene (5.3–11.5%) as main constituents. Monoterpene hydrocarbons were the most represented compounds in the oils of the plant samples collected during the flower‐budding and full‐flowering periods. On the contrary, during the fruiting stage, the oils were dominated by phenylpropanoids. The essential oils were subject of considerable variation in their composition during the various developmental stages, particularly concerning the content of myrcene that decreased significantly passing from the vegetative to the fruiting stage. Conversely, for myristicin, the opposite trend was observed. Furthermore, the essential‐oil yields were quite low during the flower‐budding phase (0.27%), but rapidly increased during plant development (0.63 and 0.68% for the flowering and fruiting phases, resp.).     

丁香挥发油化学成分与抗菌活性研究

利用气相色谱—质谱(GCMS)法结合化学计量学方法对丁香挥发油化学成分进行了分析研究。得益于化学计量学分辨方法,从丁香花蕾与丁香果实中共鉴定了46种化合物。其中从丁香果实挥发油中鉴定了41种化合物,占挥发油总量的94.154%;从丁香花蕾挥发油中鉴定出30种化合物,占其挥发油总量的98.418%。2,3,4trimethoxyacetophenone和2methoxy4[2propenyl]phenolacetate为首次从丁香挥发油中鉴定得到。两种已经确认具有生物活性的化合物丁子香酚和石竹烯在丁香果挥发油分别为22.667%和7.147%,而在丁香花蕾挥发油中含量分别为和57.133%和14.408%,二者在相对含量上差异较大。体外抗菌试验结果表明,这两种挥发油对金黄色葡萄球菌和白色念珠菌十分敏感,对大肠杆菌和枯草杆菌敏感。而丁香花蕾挥发油对所有试验菌株都比丁香果挥发油表现出更强的抗菌活性,我们认为这可能是前者丁子香酚和石竹烯含量高的原因。     

Essential oil in Betula spp. leaves naturally growing in Estonia

The essential oils of the leaves of Betula pendula Roth., Betula pubescens Ehrh., Betula humilis Schrank and Betula nana L. (Betulaceae), and B. pendula buds were obtained using hydrodistillation and their chemical compositions were analyzed using gas chromatography and gas chromatography – mass spectrometry. The yield of essential oil was the highest (0.27%) in leaves of. B. humilis and the lowest in the leaves of B. pendula (0.11%), B. pubescens (0.05%) and B. nana (traces). Overall, 35–60 compounds were identified representing more than 92% of the total volume of the oils investigated. The bicyclical sesquiterpenoids found in the essential oils extracted from the leaves of B. pendula, B. pubescens and B. humilis and from the buds of B. pendula where α-betulenol (20.4–33.1%), α-betulenol acetate (5,6–28.9%), β-betulenal (5.5–6.2%) and β-betulenol (2.0–5.8%). The buds of B. pendula contained more birkenal, (E)-β-caryophyllene, δ-cadinene and caryophyllene oxide, but less α-betulenol acetate, β-betulenal and aliphatic compounds than the oils extracted from the leaves investigated. The oil composition of B. humilis and B. nana leaves was studied for the first time. The content of essential oil of B. nana leaves was much more varied: the oil contained less bicyclical sesquiterpenoids and more aliphatic compounds than the other Betula species investigated. The findings of our study could be used in chemosystematics of birch species, especially for B. nana.     

Phytochemical Analysis and in vitro Free‐Radical‐Scavenging Activities of the Essential Oils from Leaf and Fruit of Melaleuca leucadendra L.

The phytochemical profile of Melaleuca leucadendra L. leaf and fruit oils from Cuba was investigated by GC and GC/MS. Forty‐one and sixty‐four volatile compounds were identified and quantified, accounting for 99.2 and 99.5% of the leaf‐oil and fruit‐oil total composition, respectively. The main components were 1,8‐cineol (43.0%), viridiflorol (24.2%), α‐terpineol (7.0%), α‐pinene (5.3%), and limonene (4.8%) in the leaf oil, and viridiflorol (47.6%), globulol (5.8%), guaiol (5.3%), and α‐pinene (4.5%) in the fruit oil. The antioxidant capacity of these essential oils was determined by three different in vitro assays (2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radical, thiobarbituric acid reactive species (TBARS), and 2,2′‐Azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) (ABTS) radical cation), and significant activities were evidenced for all of them.     

大花金挖耳不同部位挥发油化学成分比较分析

采用GC-MS技术,对利用水蒸气蒸馏法从大花金挖耳根、茎、叶、花及花托等5个部位获得的挥发油组分进行了分析.从大花金挖耳5种挥发油中共鉴定出99种成分,从根、茎、叶、花及花托分别鉴定出了37、34、47、29和40种化合物,已鉴定的组分分别占相应挥发油的85.86%、84.98%、83.06%、84.58%和89.06%.5个部位挥发油化学组成差异较大,根挥发油主要成分为倍半萜类和酯类;茎挥发油主要为倍半萜和烯类(包括烯醇、烯酸、烯酮);叶和花挥发油主要为烯类(包括烯醇、烯酸、烯酮)和酯类;花托挥发油主要为倍半萜类和二萜类.