Volatile Composition and Biological Activity of Jordanian Commercial Samples of R. coriaria L. Fruits.

The present paper reports the GC-HS-SPME analysis of volatile emission and GC-MS analysis of chemical composition of essential oil of R. coriaria fruits of eight different samples of R. coriaria L. fruits ("sumac" folk name), collected from Jordanian agricultural field and the local market. The analyses show an important variability among the Sumac samples probably due to the origin, cultivation, harvesting period, drying, and conservation of the plant material. The main class of component present in all samples was monoterpenes (43.1 to 72.9%), except for one sample which evidenced a high percentage of sesquiterpene hydrocarbons (38.5%). The oxygenated monoterpenes provided a contribution to total class of monoterpenes ranging from 10.1 to 24.3%. A few samples were rich in monoterpene hydrocarbons. Regarding the single components present in all the volatile emissions, ß-caryophyllene was the main compound in most of the analyzed samples, varying from 34.6% to 7.9%. Only two samples were characterized by α-pinene as the main constituent (42.2 and 40.8% respectively). Essential oils were collected using hydro-distillation method. Furfural was the main constituent in almost all the analyzed EOs (4.9 to 48.1%), except in one of them, where ß-caryophyllene was the most abundant one. ß-caryophyllene ranged from 1.2 to 10.6%. Oxygenated monoterpenes like carvone and carvacrol ranged from 3.2-9.1% and 1.0-7.7% respectively. Cembrene was present in good amount in EO samples EO-2 to EO-8. The antioxidant capacities of the fruit essential oils from R. coriaria were assessed using spectrophotometry to measure free radical scavenger 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical and inhibition of ß-carotene bleaching (BCB). The essential oils from the fruits of the different samples of R. coriaria exhibited the MIC value ranging from 32.8 to 131.25 µg/mL against S. aureus ATCC 6538 and 131.25 to 262.5 µg/mL against E. coli ATCC 8739. The MIC values of ciprofloxacin were 0.59 and 2.34 µg/mL against S. aureus ATCC 6538 and E. coli ATCC 8739, respectively.

Soil and Leaf Nutrients Drivers on the Chemical Composition of the Essential Oil of Siparuna muricata (Ruiz & Pav.) A. DC. from Ecuador.

Chemical compositions of plants are affected by the initial nutrient contents in the soil and climatic conditions; thus, we analyzed for the first time the effects of soil and leaf nutrients on the compositions of the essential oils (EOs) of Siparuna muricata in four different localities in Ecuador. EOs were obtained by hydrodistillation and analyzed by gas chromatography/mass spectrometry (GC/MS) and a gas chromatography/flame ionization detector (GC/FID). Enantiomeric distribution by GC/MS was determined, modifying the enantiomeric separation of ß-pinene, limonene, δ-elemene, ß-bourbonene, cis-cadina-1 (6), 4-diene and atractylone. A total of 44 compounds were identified. The most representative for L1 were guaiol, atractylone and 4-diene; for L2, cis-cadina-1(6),4-diene and myrcene; for L3, atractylone, myrcene and germacrene B; and finally, L4 germacrene B, myrcene and cis-cadina-1(6),4-diene. Correlations between soil- leaf chemical elements such as Al, Ca, Fe, Mg, Mn, N and Si in the different localities were significant with chemical composition of the essential oil of Siparuna muricata; however, correlations between soil and leaf K, P, and Na were not significant. Cluster and NMDS analysis showed high dissimilarity values of secondary metabolites between four localities related with changes in soil- leaf nutrients. Thus, the SIMPER routine revealed that not all secondary metabolites contribute equally to establishing the differences in the four localities, and the largest contributions are due to differences in guaiol, cis-cadina-1(6),4-diene, atractylone and germacrene. Our investigation showed for the first time the influences of altitude and soil- leaf chemical elements in the chemical composition of the EOs of S. muricata.

Essential Oils of New Lippia alba Genotypes Analyzed by Flow-Modulated Comprehensive Two-Dimensional Gas Chromatography (GC×GC) and Chemometric Analysis.

Lippia alba (Mill.) N. E. Br. (Verbenaceae) is an aromatic shrub whose essential oils have stood out as a promising source for application in several industrial fields. In this study, the essential oils chemical characterization of eight new L. alba genotypes was performed. The selected materials were collected from the Active Germplasm Bank of the Agronomic Institute and the essential oils were extracted by hydrodistillation. Flow-modulated comprehensive two-dimensional gas chromatography coupled to mass spectrometry (GC×GC-MS) was employed for chemical characterization and evaluation of possible co-eluted compounds. In addition, the chemical analyses were submitted to multivariate statistical analyses. From this investigation, 73 metabolites were identified in the essential oils of the genotypes, from which α-pinene, ß-myrcene, 1,8-cineole, linalool, neral, geranial, and caryophyllene oxide were the most abundant compounds among the accessions. This is the first report disclosing α-pinene in higher amounts in L. alba (19.69%). In addition, sabinene, trans-verbenol, myrtenol, (E)-caryophyllene, α-guaiene, germacrene D, and α-bulnesene were also found in relevant quantities in some of the genotypes, and myrtenal and myrtenol could be well separated through the second dimension. Such results contributed to the understanding of the chemical composition of those new genotypes, being important to drive a future industrial applicability and studies in genetic breeding.

Chemical composition of essential oils from the underground parts of Glycyrrhiza echinata L. accessions growing wild in Northern Iran.

Glycyrrhiza echinata L. is a perennial plant of considerable commercial importance in medicine, pharmaceuticals, cosmetics, and tobacco industries and the production of food additives as flavoring and sweetening agent. This study, variation on composition and yield of essential oil from the underground parts of five accessions of G. echinata growing wild in northern Iran was investigated. Results showed high variability for the main constituents of essential oil among accessions of G. echinata. The presence of α-pinene and myrcene in two accessions suggests that these volatiles could serve as chemotaxonomic markers and also might be considered as potentially relevant for taste. The presence of ß-caryophyllene and α- caryophyllene in three accessions could be strong potential for being used in medical applications (anticancer and analgesic properties). Generally, the essential oils from G. echinata and other species could be very competitive targets for phytochemical and food studies.

Evaluation of dynamic changes in the bioactive components in Citri Reticulatae Pericarpium (Citrus reticulata 'Chachi') under different harvesting and drying conditions.

BACKGROUND: The Citrus reticulata 'Chachi' pericarp (CRCP) is one cultivar of Citri Reticulatae Pericarpium (Chenpi), which is widely applied in medicine and food. To determine the potential value of CRCP harvested at different stages and subjected to different drying processes, the dynamic changes in the bioactive components were profiled and evaluated in this study. RESULTS: The contents of all non-volatile components, i.e. synephrine, limonin, phenolic acids and flavonoids, decreased with delayed harvest time. The volatiles thujene, α-pinene, ß-pinene, d-citronellol, d-citronellal, decanal, linalool, geraniol, l-cis-carveol, terpinen-4-ol, α-terpineol, carvacrol, perillaldehyde, methyl 2-(methylamino)benzoate and d-limonene were considered the characteristic components for distinguishing CRCP harvested at different stages. Phenolic acids, synephrine and limonin were stable at different drying temperatures; however, high-temperature drying at 60 °C induced a significant transformation in the flavonoids (especially polymethoxyflavones) and volatile substances in CRCP. CONCLUSIONS: The results suggested that most of the bioactive components declined with the growth of Citrus reticulata 'Chachi'. And it is believed that the fresh peel should be naturally sun-dried or dried at low temperature (30 or 45 °C) rather than at high temperature (60 °C) to prevent excessive loss of nutrients. © 2020 Society of Chemical Industry.

α-Pinene odor exposure enhances heat stress tolerance through Daf-16 in Caenorhabditis elegans.

Aromatherapy has been widely used as complementary and alternative medicine to reduce pain and induce sleep. However, the scientific evidence regarding the biological effects of odor is scarce and the underlying molecular mechanisms have not been clarified. We treated worms with contactless S-(-)- and R-(+)-α-pinene and analyzed heat stress tolerance. Odor stimulation induced motility recovery after incubation at 35 °C for 4 h. This increase in heat stress tolerance was not present in odr-3 mutants and daf-16 mutants. S-(-)- and R-(+)-α-pinene expanded health span and increased fat accumulation. Moreover, S-(-)- and R-(+)-α-pinene modulated the expression of 84 and 54 genes, respectively. These results show that α-pinene odor stimulation is related to stress tolerance, lipid metabolism, and health span via some specific signaling pathways. This study may provide a potential target for antiaging and disease prevention.

A rapid GC-FID method for determination of sabinene, ß-pinene, α-thujone and ß-thujone in the essential oil of Kitchen Sage (Salvia officinalis L.).

Terpenes and terpenoids are dominant fragrances in the essential oils of many economically important fruits and vegetables. Hence, content and variation are important factors in the evaluation and common perception of food quality. Sabinene, ß-pinene, α-thujone and ß-thujone are examples of such compounds found in the different species of Sage. Sabinene and ß-pinene are spicy compounds much used by the fragrance industry while the two thujones are highly toxic. Here, we report a rapid method for quantification of these compounds in the essential oil of Sage. The total analytical time is approx. 7,5 min in contrast to approx. 30 min for similar gas chromatographic methods. The analytical method had a linear range of 28-342 mg L-1 for the different compounds, with an analytical precision of 0,6-0,9% for standards. Correlation coefficients were 0,9993-1,0000. The Limit of Detection of all compounds were 0,02-0,9 mg L-1 and the Limit of Quantification were 0,08-3,0 mg L-1. The technique was used for quantification of the compounds in seven commercial essential Sage oils and in a pilot study of the effect of ozone on the terpenes and terpenoids in fresh Sage leaves. Large variation was observed between the different commercial samples, of which some were thujone dominant and some did not have any content of thujone at all. Treatment of fresh Sage leaves with ozone caused degradation of the terpenes sabinene and ß-pinene whereas the terpenoids α/ß-thujone were more resistant to degradation.

Components of Volatile Fractions from Eucalyptus camaldulensis Leaves from Iraqi-Kurdistan and Their Potent Spasmolytic Effects.

Inhalation of vapors from a hot tea of Eucalyptus camaldulensis Dehnh. leaves is considered by Iraqi-Kurdistan people an effective spasmolytic and antipyretic remedy for the treatment of respiratory diseases. The constituents of volatile fractions isolated by hydrodistillation from dried leaves of the plant collected in Kurdistan were determined by GC-FID and GC-MS analyses. More than 90% components were identified. The most abundant constituents were 1,8-cineole, p-cymene, α-pinene, terpinen-4-ol, aromadendrene, and α-terpineol. The different volatile fractions induced relaxation on rat isolated aortic and tracheal rings in concentration-dependent manner. These effects appeared to be due to a complex interaction between various terpenoid components rather than being only due to the main oil constituent, 1,8-cineole. The KCa channel and the NO pathway were not significantly involved in the relaxation mechanism, while Ca2+ channels played a major role in the spasmolytic effects.

Influence of cultivar and technological conditions on the volatile profile of virgin pistachio oils.

The main aim of this work was to characterize the volatile profile of virgin pistachio oils produced from eight cultivars (Aegina, Avdat, Kastel, Kerman, Larnaka, Mateur, Napoletana and Sirora), under different technological conditions (temperature, roasting, use of whole nuts, screw speed and nozzle diameter), and compare it with those of commercial pistachio oils. Terpenes (15.57-41.05 mg/kg), accounting for ~97% of total volatiles, were associated with appreciated sensory properties, with α-pinene as the main volatile (14.47-37.09 mg/kg). Other terpene compounds such as limonene (0.11-3.58 mg/kg), terpinolene (0.00-1.61 mg/kg), ß-pinene (0.12-1.20 mg/kg) and α-terpineol (0.00-1.17 mg/kg) were quantified at lower concentrations. Acids, alcohols, aldehydes, esters and hydrocarbons only summed to ~3% of the total volatile compounds. The volatiles content greatly depended on the pistachio cultivar employed. The influence of extraction conditions was also very relevant; in particular, terpenes doubled (28.38-53.84 mg/kg) using whole pistachios for oil extraction, also being incremented by mild processing conditions. On the contrary, higher temperature or roasting decreased the terpene content (~50-25% respectively), and pyrazines appeared (up to 3.12 mg/kg).

Essential oil and fractions isolated of Laurel to control adults and larvae of cattle ticks.

This study, was to evaluate the acaricidal effect of the essential oil (EO) and fractions (FR) obtained from Laurus nobilis leaves on Rhipicephalus (Boophilus) microplus. Eight fractions were obtained, however FR1: sabinene (37.83%), ß-pinene (13.50%), 1,8-cineole (12.66%), α-pinene (12.56%) and FR8: α-terpineol (79.19%) were highlighted as to the larvicidal potential when submitted by Larval Packet Test. The EO was tested by the Adult Immersion Test, at concentrations of 200.00; 100.00 and 50.00 µL/mL caused mortality of engorged females, egg mass reduction and hatching inhibition. Two fractions are shown to be efficient in controlling larvae FR8 (LC50 = 0.13 µL/mL, LC99 = 0.51 µL/mL) and FR1 (LC50 = 0.20 µL/mL, LC99 = 0.56 µL/mL). The fractionation of EO was determinant to elucidate which compounds were responsible for the larvicidal potential. This study opens new perspectives to direct new bioassays with the compounds obtained in the fractionation, since they present high potential on cattle tick larvae.

Chemical composition of the essential oils and headspace volatiles of Ferulago sylvatica (Besser) Reichenb. from Serbia.

Chemical composition of the headspace volatiles and essential oils isolated from different parts of Ferulago sylvatica was determined by GC and GC/MS analyses. The results showed that headspace volatiles obtained from the aerial parts and roots were similar regarding the number of identified compounds and main components. However, essential oils obtained from different plant organs showed significant differences in chemical composition. Myrcene was the most abundant component of the inflorescences and shoots volatiles, while α-pinene make up over 50% of the root volatiles. Only three components were identified in the root essential oil with 2,3,6-trimethyl benzaldehyde (92.7%) as the main component. In the shoots sample the terpenoid fractions represented 56% of the oil, unevenly distributed between monoterpenoids and sesquiterpenoids with germacrene D (32.5%) recognized as the main constituent. On the other hand, more than 94% of the inflorescences oils were monoterpenoids with myrcene as the most abundant contributor (29.2%).

Comparative efficacy of Eucalyptus globulus (Labill) hydrodistilled essential oil and temephos as mosquito larvicide.

In this study Eucalyptus globulus essential oil was tested on major mosquito species and toxicity was compared with temephos. Mortality was calculated after 24 h and 48 h post treatment. In 24 h treatment essential oil show strong larvicidal activity with LC50 and LC90 values were 30.198ppm, 103.389ppm for Anopheles stephensi, 13.578ppm, 106.755ppm for Aedes aegypti; and, 7.469ppm, 32.454ppm for Culex quinquefasciatus and 48 h post treatment LC50 and LC90 values were, 12.576, 49.380ppm for Anopheles stephensi, 7.926, 34.470ppm for Aedes aegypti and 4.408, 21.048ppm for Culex quinquefasciatus. Chemical composition of essential oil using GC-MS and FT-IR analysis shows the presence of 1,8-cineol, (71.7%); α-pinene, (9.14%) as a major compounds. Our findings suggest that essential oil from Eucalyptus globulus leaves can be used for control of mosquito larvae.

Effect of essential oil from Ageratum fastigiatum on beta-integrin (CD18) expression on human lymphocytes stimulated with phorbol myristate acetate in vitro.

Agareratum fastigiatum is a Brazilian medicinal plant used as anti-inflammaroty and for wound healing by the folk medicine. In vitro and in vivo studies involving A. fastigiatum essential oil (EOAF) showed indications of anti-inflammatory activity, however, its effect on membrane integrins involved on cell migration is still unclear. Hence, it was evaluated in the present study the effect of EOAF on CD18 frequency on human lymphocytes. By using gas chromatography/mass spectrometry it was identified 9 compounds on EOAF: α-pinene; ß-pinene; ß-myrcene; d-limonene; ß-ocimene; sesquiterpenes; α-copaene; 4,8-ß-epóxi-caryophyllene; germacrene and bicyclogermacrene. On in vitro tests, 6.25 × 10-3 and 12.5 × 10-3 µL/mL EOAF reduced CD18 frequency on phorbol-12-myristate-13-acetate (PMA)-stimulated lymphocytes. Such cells were obtained from peripheral blood of healthy volunteers, and were treated or not with EOAF. They were stained with fluorescent anti-CD18 monoclonal antibodies, after 24 hours incubation. Our data corroborates previous findings, indicating a possible anti-inflammatory activity of EOAF.

Variations of peel essential oils during fruit ripening in four lemon (Citrus limon (L.) Burm. F.) cultivars.

BACKGROUND: Lemon processing procedures yield a significant amount of waste as peels, which are 57% of processed lemons and represent a possible source of bioactive compounds (essential oils, EOs). EOs were extracted from lemon fruits belonging to four cultivars harvested at four different sampling times (25 October, 23 November, 20 December, 1 February), characterized, and quantified through gas chromatography-mass spectrometry. RESULTS: The chemical composition of EOs highlighted that 26 compounds of the four lemon cultivars at the different ripening stages were clearly identified. The compounds analysed belonged to four chemical classes: monoterpene hydrocarbons, oxygenated monoterpenes, sesquiterpenes, and fatty alcohol esters. Among the monoterpene hydrocarbons, d-limonene, ß-pinene, and γ-terpinene were the most abundant; and among the oxygenated monoterpenes, α-terpineol, nerol, and geraniol were the most abundant. Quantitative gas chromatography-mass spectrometry analysis of the most abundant monoterpene hydrocarbons (α-pinene, ß-pinene, myrcene, d-limonene, and γ-terpinene) highlighted that the amount of EOs decreased during ripening stages. 'Ovale di Sorrento' and 'Sfusato Amalfitano' showed the highest level of EOs in December, whereas in 'Femminello Cerza' and 'Femminello Adamo' this occurred in November. EOs, as well as the phenolic compounds, were positively correlated with the antioxidant activity (2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid). CONCLUSIONS: EOs reached the highest level in the four lemon cultivars at different ripening stages. Campanian cultivars ('Ovale di Sorrento' and 'Sfusato Amalfitano') showed the greatest EO content in November, whereas in Sicilian cultivars ('Femminello Cerza' and 'Femminello Adamo') this occurred in December. Besides phenolic compounds, measured in lemon peel extracts, EOs can contribute to antioxidant activity, as demonstrated by the positive correlation. © 2019 Society of Chemical Industry.

Sedative effects of the essential oil from the leaves of Lantana camara occurring in the Republic of Benin via inhalation in mice.

Lantana camara Linn. (Verbenaceae) is used traditionally for its numerous medicinal properties such as antimalarial, antibacterial, anticancer and anti-inflammatory. In the present study, we investigated the chemical composition of essential oil from the leaves of L. camara (LCEO) occurring in the Republic of Benin (West Africa) in comparison with LCEOs from other regions; evaluated its sedative effects in mice via inhalation administration; and identified the compounds responsible for activity. LCEO was extracted by hydrodistillation and chemical analyses of the oil were performed by GC and GC/MS. The oil was dominated by monoterpene hydrocarbons (60.58%) and oxygenated monoterpenes (33.39%), among which sabinene (38.81%) and 1,8-cineole (28.90%) were the most abundant. LCEO administered via inhalation to mice significantly decreased locomotor activity in a dose-dependent manner, mainly at the doses of 0.0004 and 0.04 mg per 400 µL of triethyl citrate (TEC). The oil was fractionated to give two fractions, which were further investigated, and revealed that both sabinene and 1,8-cineole were the principal active compounds. The results of the present study indicated that via inhalation administration, LCEO and its main constituents could be considered as promising candidates for the management of dementia, insomnia, attention deficit hyperactivity disorder and other central nervous system-associated diseases.

Influence of environmental factors on the volatile composition of two Brazilian medicinal plants: Mikania laevigata and Mikania glomerata.

INTRODUCTION: Mikania laevigata Sch.Bip. ex Baker and Mikania glomerata Spreng. are medicinal plants popularly known as guaco, used for inflammatory diseases of the respiratory system, included in pharmaceutical formularies and often used without distinction. However, several studies show that the chemical composition varies between these species, as well as in plants are subjected to different environmental stresses. Few studies have been carried out with the volatile compounds of guaco, even less about the changes in volatile composition due to abiotic variation. OBJECTIVE: The aim of this work was to evaluate how volatile compounds vary according to the seasons and at different times of the day and if these compounds are influenced by the variations in the growth conditions such as: temperature, luminosity and water. METHODS: The headspace volatiles of the leaves were sampled by solid phase micro extraction and analyzed by gas chromatography-mass spectrometry. Untargeted metabolomic analysis of the resulting chromatograms and chemometrics was applied. The chemical profile of the volatiles of M. laevigata and M. glomerata were different; being clearly separated in the exploratory grouping analyzes (PCA), followed by analysis of variance of the marker compounds of both species. RESULTS: Only M. laevigata contained coumarin, considered to be the chemical marker of both species and to be responsible for the therapeutic activities. There was no significant difference between the morning and afternoon collections of either species. Coumarin, α-pinene and bicyclogermacrene were more intense in the volatiles of M. laevigata throughout the year and responsible for grouping the samples of this species. For M. glomerata, hexanal and 2-hexenal were responsible for grouping the samples and were more intense in all months. The growth conditions tested affected the intensity of specific compounds in the chromatograms. Some compounds were less intense with the increase of the temperature and in the plants subjected to full sunlight. However, certain volatile compounds-such as pinenes-were more intense in plants suffering drought. CONCLUSION: The variation in composition between species of guaco was greater than those observed in the seasonal and cultivation studies, indicating that these species cannot be used indistinctly.