Chemical Variability of the Berry Essential Oil of Two Subspecies of Juniperus Oxycedrus L. from Northwestern Algeria.

The chemical composition of 33 oil samples isolated from the berries of individual trees of two subspecies of Juniperus oxycedrus L., collected in four locations in Tlemcen and Aïn Temouchent provinces, was investigated by GC-FID, GC/MS and 13CNMR. In total, 83 compounds were identified, accounting for 85.9 % to 98.6 % of the total composition. Yields ranged between 0.02 and 0.40 % (w/w). All compositions were submitted to statistical analysis. Combination of hierarchical clustering dendrogram and principal component analysis suggested the existence of two groups, the second group being sub-divided into two sub-groups. Groups and sub-groups were distinguished with respect to their contents of α-pinene, germacrene D, myrcene and, to a lesser extent, of manoyl oxide. The chemical composition of the oils belonging to subsp. oxycedrus was largely dominated by monoterpenes. α-Pinene (23.7-63.2 %) and germacrene D (4.5-25.4 %) were the major components, followed by myrcene (3.1-16.7 %). Conversely, samples oils of subsp. macrocarpa were largely dominated by germacrene D (4.4-30.0 %), followed by a lower content of α-pinene (10.0-24.3 %) and myrcene (1.0-4.3 %) and a significant content of manoyl oxide (4.3-9.9 %).

Chemical Variability and Anti-Inflammatory Activity of Rosmarinus officinalis L. Leaf Essential Oil from Algerian Sahara.

The chemical composition of 71 oil samples from the leaves of Rosmarinus officinalis L., harvested in three provinces: Naâma (Western Algeria), Béchar and Adrar (Algerian Sahara), was investigated by GC-FID, GC/MS and 13CNMR. In total, 52 compounds were identified accounting for 88.8 % to 99.9 % of the total composition. The chemical composition of the oils was largely dominated by monoterpenes, with 1,8-cineole (9.7-70.2 %), camphor (0.3-31.0 %) being the major compounds followed by borneol (0.3-21.0 %), α-pinene (4.5-14.5 %), ß-pinene (0.1-12.0 %), linalool (0.7-9.9 %) and verbenone (up to 11.1 %) which was present only in the samples harvested in Adrar. All compositions (71 samples) were submitted to statistical analysis. Combination of hierarchical clustering dendrogram and principal component analysis suggested the existence of three groups (one of these being subdivided into two sub-groups) which were distinguished on the basis of 1,8-cineole, camphor and verbenone contents. Four essential oil samples, containing 1,8-cineole and/or camphor as main components, exhibited anti-inflammatory activity against lipoxygenase, with IC50 values in the range 93 to 155 µg/mL.

Phytochemical, Morphological, and Physiological Variation in Different Ajowan (Trachyspermum ammi L.) Populations as Affected by Salt Stress, Genotype × Year Interaction and Pollination System.

In the present research, 28 populations of ajowan (Trachyspermum ammi L.) were evaluated for agro-morphological traits and essential oil yield in two consecutive years. Then, selected ajowan populations from these two years were used for further morphophysiological and biochemical studies under different salinity levels (control, 60, 90, and 120 mM NaCl). The main components of the oil were thymol (32.7-54.29%), γ-terpinene (21.71-32.81%), and p-cymene (18.74-26.16%). Salt stress caused an increase in essential oil content in the Esfahfo and Qazvin populations. The highest total phenolic and flavonoid contents were found in the Arak population grown in 60 mM NaCl (183.83 mg TAE g-1 DW) and the Yazd population grown in 90 mM NaCl (5.94 mg QE g-1 DW). Moreover, the Yazd population exhibited the strongest antioxidant activity based on DPPH (IC50 = 1566 µg/mL) under 60 mM NaCl and the highest reducing power (0.69 nm) under 120 mM NaCl. The results revealed that low and moderate salt stress improves the phytochemicals of ajowan seeds, which are useful for pharmaceutical and food applications. In this research, some morphological traits, as well as essential oil yield, were evaluated in open pollinated versus self-pollinated plants. As a result, plant height, number of flowering branches, and crown diameter significantly decreased in some populations, while a significant increase was obtained for number of flowers per umbel and seed numbers per umbel. Finally, self-pollination of ajowan might provide new insights for further breeding programs to increase oil or thymol content in ajowan.

A Study of the Chemical Composition, Antioxidant Potential, and Acute Toxicity of Bulgarian Tanacetum vulgare L. Essential Oil.

Common tansy (Tanacetum vulgare L.) is a plant with medicinal properties that has traditionally been used in folk medicine for its anthelmintic, antispasmodic, and choleretic effects, for the treatment of diarrhea and digestive problems, and externally, as an insecticide in veterinary practices. In the current study, we investigated, for the first time, the chemical profile and antioxidant activity of essential oil from a wild population of T. vulgare L. growing in Bulgaria. Common tansy essential oil (EO), which is rich in bicyclic monoterpenes, was obtained using hydrodistillation and characterized by using gas chromatography-mass spectrometry (GC-MS). Thirty-seven compounds were identified in Bulgarian tansy EO. Among the major constituents were oxygenated monoterpenes, including compounds such as camphor (25.24%), trans-chrysantenyl acetate (18.35%), cis-verbenol (10.58%), thujone (6.06%), eucaliptol (5.99%), and α-campholenal (5.98%). The analysis results identified the essential oil from T. vulgare L. grown in the western Rhodope Mountains of Bulgaria as the camphor chemotype. Furthermore, its antioxidant activity was analyzed using the oxygen radical absorbance capacity (ORAC) method and was found to be 605.4 ± 49.3 µmol TE/mL. The essential oil was also tested for single-dose acute toxicity on Wistar rats and was found to be non-toxic by oral administration. The mean lethal dose by intraperitoneal administration was LD50 i.p. = 14.9 g/kg body weight. The results of the conducted study can serve as a basis for the evaluation and subsequent exploration of other pharmacotherapeutic effects of the essential oil obtained from the inflorescences of the Bulgarian species T. vulgare L.

Essential Oil Composition and Enantioselective Profile of Agastache urticifolia (Lamiaceae) and Monardella odoratissima (Lamiaceae) from Utah.

Two species within the Lamiaceae (mint) family, Agastache urticifolia and Monardella odoratissima, are aromatic plants that are native to the Intermountain Region (USA). Essential oil produced through steam distillation was examined to establish the essential oil yield and both the achiral and chiral aromatic profiles of both plant species. The resulting essential oils were analyzed by GC/MS, GC/FID, and MRR (molecular rotational resonance). For A. urticifolia and M. odoratissima, achiral essential oil profiles were largely composed of limonene (71.0%, 27.7%), trans-ß-ocimene (3.6%, 6.9%), and pulegone (15.9%, 4.3%), respectively. Between the two species, eight chiral pairs were analyzed and, interestingly, the dominant enantiomer (calculated as ee%) of limonene and pulegone switched between the two species. Where enantiopure standards were not commercially available, MRR was used as a reliable analytical technique for chiral analysis. This study verifies the achiral profile for A. urticifolia and, for the first time to the authors' knowledge, establishes the achiral profile for M. odoratissima and chiral profile for both species. Additionally, this study confirms the utility and practicality of using MRR for determining chiral profiles in essential oils.

A comparison of the performance of conventional and eco-friendly extraction methods in the evaluation of total phenolics, antioxidant activity, and chemical composition of anise.

In this work, the essential oil of Pimpinella anisum seeds was obtained by six different extraction methods. In the chemical composition analysis, 4, 6, 4, 1, 20, and 8 compounds were detected in the extracts obtained by Soxhlet, Ultrasonic-assisted (UAE), hydrodistillation using Clevenger apparatus (HDC), subcritical water extraction (SWE), supercritical carbon dioxide extraction (ScCO2) using three solvents (methanol (ScCO2-Met), ethanol (ScCO2-Et), and hexane (ScCO2-H)) and supercritical 1,1,1,2-tetrafluoroethane (ScR134a) methods, respectively. Also, the performances of the applied methods were compared by analysing the total phenolic content (TPC) and antioxidant activity of the extracts. Anethole was the main component of all extracts obtained by SWE (94.5%) and Soxhlet (94.5%) methods, respectively. Also, TPC values were the highest (508.5 mg GAE/100 g kb) in ScR134a extract and the lowest (27.77 mg GAE/100 g kb) in HDC extracts. The antioxidant capacity was found to be the highest in ScCO2-H (IC50 = 1.58 mg/mL) and the lowest in Soxhlet extracts (IC50 = 0.07 mg/mL). The results showed the great effectiveness of eco-friendly extraction SWE, ScCO2-Et, and ScR134a methods.

Essential oil composition and biological activities of Aleppo pine (Pinus halepensis Miller) needles collected from different Tunisian regions.

The aim of this research was to investigate the variation regarding the chemical composition and biological activities of needles essential oils (EOs) of P. halepensis. Chemical profiles demonstrated a significant (P < 0.05) variability among the different EOs. The main identified compounds were caryophyllene (48.77 ± 2.26), phenyl isovalerate (22.22 ± 2.26), ß-myrcene (15.55 ± 5.65) and α-pinene (14.52 ± 2.26). Further, it was shown that EO from Tabouba (Tab) displayed the highest DPPH scavenging (IC50 = 73.03 mg/mL), anti-inflammatory (IC50 = 23.29 µg/mL) and α-glucosidase inhibition activities (IC50 = 254.45 µg/mL). While Elmahres (Elm) exhibited the most potent ABTS radical's inhibition (IC50 = 197.87 mg/mL). For the cytotoxic capacities, Kettana (Ket) was the most efficient against breast cancer MCF-7 cell line with IC50 value better than doxorubicin used as positive control. Obtained results suggest that EO of P. halepensis could be used as a source of bioactive compounds.

Growth, oil and physiological parameters of three mint species grown under saline stress levels.

Salinity stress is known to have a detrimental effect on mint plants. The aim of the present work was to investigate the possible effects of salinity stress on Mentha spicata, Mentha piperita and Mentha arvensis. Plants were exposed to salinity stress using different concentrations of NaCl (0, 50, 100, 150 mM). Under salinity stress, plant growth, oil yield, content and composition, as well as physiological parameters were adversely affected. Among the studied species, M. arvensis experienced the maximum loss in terms of oil percentage. Physiological characteristics and oil composition were significantly affected with intensification of salt stress. For instance, in M. spicata, with increasing salinity stress, piperitone oxide was decreased from 78.4% in control to 38.0% in 150 mM NaCl, whereas menthol was increased from 1.0 to 37.1%. Moreover, in M. piperita, menthone, isomenthone and limonene were all increased in low stress and then were decreased in high stress conditions. In M. arvensis, the major compound; menthol was not affected but the content of menthone increased. It could be concluded that the salinity stress is detrimental but might be useful and may be recommended as an appropriate approach in improving the oil quality or to producing specific compounds under mild or moderate stress.

Seasonal Variation in the Essential Oil Yield and Composition of Cinnamomum parthenoxylon (Jack) Meisner.

Cinnamomum parthenoxylon (Jack) Meisner is an important natural aromatic plant because its leaves are rich in essential oil. Linalool chemotype C. parthenoxylon was used as the research material in the present study. The leaf essential oil yield, the main chemical components, and their content were measured every month from January to December 2018 to study the seasonal variation in the yield and chemical components of C. parthenoxylon leaf essential oil. The results revealed that the essential oil yield and the main chemical component linalool in the essential oil of C. parthenoxylon leaves showed significant differences among months. The leaf essential oil yield and linalool content decreased to the lowest in March and increased rapidly from April to May. The leaf essential oil yield was the highest in May, and a relatively high yield was maintained from April to August. The linalool content in leaf essential oil was stable in other months except March. The leaf essential oil yield of C. parthenoxylon had a very significant positive correlation with monthly rainfall and monthly average temperature. Intense rainfall and high monthly average temperature were conducive to the synthesis and accumulation of C. parthenoxylon leaf essential oil. This study provided a theoretical basis for cultivating C. parthenoxylon as a raw material for spices and determining the best harvest time.

Seasonal Variability of a Caryophyllane Chemotype Essential Oil of Eugenia patrisii Vahl Occurring in the Brazilian Amazon.

Eugenia patrisii Vahl is a native and non-endemic myrtaceous species of the Brazilian Amazon. Due to few botanical and phytochemical reports of this species, the objective of the present work was to evaluate the seasonal variability of their leaf essential oils, performed by GC and GC-MS and chemometric analysis. The results indicated that the variation in oil yields (0.7 ± 0.1%) could be correlated with climatic conditions and rainy (R) and dry seasons (D). (E)-caryophyllene (R = 17.1% ± 16.0, D = 20.2% ± 17.7) and caryophyllene oxide (R = 30.1% ± 18.4, D = 14.1% ± 19.3) are the major constituents and did not display significant differences between the two seasons. However, statistically, a potential correlation between the main constituents of E. patrisii essential oil and the climatic parameters is possible. It was observed that the higher temperature and insolation rates and the lower humidity rate, which are characteristics of the dry season, lead to an increase in the (E)-caryophyllene contents, while lower temperature and insolation and higher humidity, which occur in the rainy season, lead to an increase in the caryophyllene oxide content. The knowledge of variations in the E. patrisii essential oil composition could help choose the best plant chemical profile for medicinal purposes.

Effects of Supplemental Light Spectra on the Composition, Production and Antimicrobial Activity of Ocimum basilicum L. Essential Oil.

This study was performed to investigate the effects of different supplemental light spectra and doses (duration and illuminance) on the essential oil of basil (Ocimum basilicum L.) cultivated in the net-house in Vietnam during four months. Ten samples of basil aerial parts were hydrodistilled to obtain essential oils which had the average yields from 0.88 to 1.30% (v/w, dry). The oils analyzed using GC-FID and GC-MS showed that the main component was methyl chavicol (87.4−90.6%) with the highest values found in the oils of basil under lighting conditions of 6 h/day and 150−200 µmol·m−2·s−1. Additional lighting conditions caused the significant differences (p < 0.001) in basil biomass and oil production with the highest values found in the oils of basil under two conditions of (1) 71% Red: 20% Blue: 9.0% UVA in at 120 µmol·m−2·s−1 in 6 h/day and (2) 43.5% Red: 43.5% Blue: 8.0% Green: 5.0% Far-Red at 100 µmol·m−2·s−1 in 6 h/day. The oils of basil in some formulas showed weak inhibitory effects on only the Bacillus subtilis strain. Different light spectra affect the biomass and essential oil production of basil, as well as the concentrations of the major components in the oil.

Essential Oils from Vietnamese Asteraceae for Environmentally Friendly Control of Aedes Mosquitoes.

Mosquitoes, in addition to being a biting nuisance, are vectors of several pathogenic viruses and parasites. As a continuation of our work identifying abundant and/or invasive plant species in Vietnam for use as ecologically friendly pesticidal agents, we obtained the essential oils of Blumea lacera, Blumea sinuata, Emilia sonchifolia, Parthenium hysterophorus, and Sphaeranthus africanus; analyzed the essential oils using gas chromatographic techniques; and screened the essential oils for mosquito larvicidal activity against Aedes aegypti and Aedes albopictus. The most active larvicidal essential oils were B. sinuata, which was rich in thymohydroquinone dimethyl ether (29.4%), (E)-ß-caryophyllene (19.7%), α-pinene (8.8%), germacrene D (7.8%), and α-humulene (4.3%), (24-h LC50 23.4 and 29.1 µg/mL) on Ae. aegypti and Ae. albopictus, respectively, and Emilia sonchifolia, dominated by 1-undecene (41.9%) and germacrene D (11.0%), (24-h LC50 30.1 and 29.6 µg/mL) on the two mosquito species. The essential oils of P. hysterophorus and S. africanus were also active against mosquito larvae. Notably, B. sinuata, P. hysterophorus, and S. africanus essential oils were not toxic to the non-target water bug, Diplonychus rusticus. However, E. sonchifolia essential oil showed insecticidal activity (24-h LC50 48.1 µg/mL) on D. rusticus. Based on these results, B. sinuata, P. hysterophorus, and S. africanus essential oils appear promising for further investigations.

Antioxidant and Toxic Activity of Helichrysum arenarium (L.) Moench and Helichrysum italicum (Roth) G. Don Essential Oils and Extracts.

Helichrysum arenarium (L.) Moench (sandy everlasting) is the only species from genus Helichrysum Mill that grows spontaneously in Lithuania. The chemical composition of the essential oils (EOs) from inflorescences and leaves of H. arenarium wild plants was analysed by GC-MS. Palmitic (≤23.8%), myristic (≤14.9%) and lauric (6.1%) acids, n-nonanal (10.4%), and trans-ß-caryophyllene (≤6.5%) were the major constituents in the EOs. For comparison, the main components in EO from flowers (commercial herb material) of H.italicum were γ-curcumene (21.5%), ß-selinene (13.6%), α-selinene (8.1%), ß-eudesmol (8.3%), and α-pinene (6.5%). Composition of H. arenarium methanolic extracts was investigated by HPLC-DAD-TOF. The main compounds were the following: luteolin-7-O-glucoside, naringenin and its glucoside, apigenin, chlorogenic acid, arenol, and arzanol. Antioxidant activity of EOs and extracts was tested by DPPH● and ABTS●+ assays. Sandy everlasting extracts exhibited significantly higher radical scavenging activities (for leaves 11.18 to 19.13 and for inflorescences 1.96 to 6.13 mmol/L TROLOX equivalent) compared to those of all tested EOs (0.25 to 0.46 mmol/L TROLOX equivalent). Antioxidant activity, assayed electrochemically by cyclic and square wave voltammetry correlated with total polyphenolic content in extracts and radical scavenging properties of EOs and extracts. The toxic activity of EOs of both Helichrysum species was evaluated using a brine shrimp (Artemia salina) bioassay. H. italicum inflorescence EO was found to be toxic (LC50 = 15.99 µg/mL) as well as that of H. arenarium (LC50 ≤ 23.42 µg/mL) oils.

New Insights into the Chemical Composition, Pro-Inflammatory Cytokine Inhibition Profile of Davana (Artemisia pallens Wall. ex DC.) Essential Oil and cis-Davanone in Primary Macrophage Cells.

Artemisia pallens Wall. ex DC., popularly known as davana, has gained considerable attention because of its unique fragrance, high economic value, and pharmacological properties. The compositional complexity of davana essential oil (DO) has been a challenge for quality control. In this study, the chemical profile of DO was developed using polarity-based fractionation and a combination of gas chromatographic (GC-FID), hyphenated chromatographic (GC/MS), and spectroscopic (Fourier-Transform Infra-Red, 1D, 2D-Nuclear Magnetic Resonance) techniques. The analysis led to the identification of ninety-nine compounds. Major components of the DO were cis-davanone (D3, 53.0 %), bicyclogermacrene (6.9 %), trans-ethyl cinnamate (4.9 %), davana ether isomer (3.4 %), spathulenol (2.8 %), cis-hydroxy davanone (2.4 %), and trans-davanone (2.1 %). The study led to identifying several co-eluting novel minor components, which could help determine the authenticity of DO. The rigorous column-chromatography led to the isolation of five compounds. Among these, bicyclogermacrene, trans-ethyl cinnamate, and spathulenol were isolated and characterized by spectroscopic methods for the first time from DO. Pharmacological profile revealed that the treatment of DO and D3 inhibited the production of pro-inflammatory cytokines (TNF-α, IL-6) induced by lipopolysaccharide (LPS) in primary macrophages without any cytotoxic effect after administration of their effective concentrations. The result of this study indicates the suitability of DO and D3 for further investigation for the treatment of chronic skin inflammatory conditions.

Essential Oils from Bolivia. XV. Herzogole, an Original Monoterpene Benzodioxole from an Essential Oil from Pentacalia herzogii (Cabrera) Cuatrec.

Over 15 years, with the support of a Canadian funding agency, the Universidad Mayor de San Simón, in Bolivia, undertook a large survey of aromatic plants of the South American country. More than a hundred species were studied under various aspects, including the production and characterization of essential oils. As part of this survey, the chemical composition of an essential oil sample obtained from Pentacalia herzogii (Asteraceae) growing wild in the High Valley region of the department of Cochabamba was determined by a combination of GC and GC-MS measurements. α-Pinene was the main constituent of this essential oil (34%), accompanied by limonene (22%) and germacrene D (7.5%) as well as an important fraction of methoxylated monoterpenoids. They were mainly isomers of thymol methyl ether, accounting for 13% of the chromatogram. A new quantitatively important compound (9%) was identified through NMR and chemical synthesis as 4-isopropyl-6-methylbenzo[d][1,3]dioxole, and designated herzogole, alongside the minor related compound 1-isopropyl-2,3-dimethoxy-5-methylbenzene. The monoterpene benzodioxole featured a distinctive green-phenolic aroma which could raise interest for fragrance use. Since these compounds were not known naturally, a biosynthetic mechanism of their formation was proposed and put in perspective to illustrate the metabolic originality of P. herzogii.

Composition, Chemical Variability and Biological Activity of Cymbopogon schoenanthus Essential Oil from Central Algeria.

Cymbopogon schoenanthus (L.) Spreng. (Poaceae) is an aromatic plant whose aerial parts and rhizome produced an essential oil with pleasant odor. A chemical variability has been observed depending of the countries where the plant grows wild, including Algeria. The chemical compositions of 24 oil samples isolated from plants harvested in Central Algeria have been investigated, to evidence homogeneity or chemical variability within a given area of harvest. Twenty of these were dominated by cis- and trans-p-menth-2-en-1-ols (22.6 %±3.6 and 14.3 %±1.7, resp.) beside four atypical compositions. Otherwise, aerial parts and rhizomes produced similar essential oils. Lastly, a fair antimicrobial activity was measured against Staphylococcus aureus strain, while the antioxidant potential was low.

Toxic, Radical Scavenging, and Antifungal Activity of Rhododendron tomentosum H. Essential Oils.

The chemical composition of eight (seven shoot and one inflorescence) essential oils (EOs) of Rh. tomentosum H. plants growing in Eastern Lithuania is reported. The plant material was collected during different phases of vegetation (from April to October). The oils were obtained by hydrodistillation from air-dried aerial parts (leaves and inflorescences). In total, up to 70 compounds were identified by GC-MS and GC (flame-ionization detector, FID); they comprised 91.0 ± 4.7%-96.2 ± 3.1% of the oil content. Sesquiterpene hydrocarbons (54.1 ± 1.5%-76.1 ± 4.5%) were found to be the main fraction. The major compounds were palustrol (24.6 ± 2.6%-33.5 ± 4.4%) and ledol (18.0 ± 2.9%-29.0 ± 5.0%). Ascaridol isomers (7.0 ± 2.4%-14.0 ± 2.4% in three oils), myrcene (7.2 ± 0.3% and 10.1 ± 1.3%), lepalol (3.3 ± 0.3% and 7.9 ± 3.0%), and cyclocolorenone isomers (4.1 ± 2.5%) were determined as the third main constituents. The toxic activity of marsh rosemary inflorescence and shoot oils samples was evaluated using a brine shrimp (Artemia sp.) bioassay. LC50 average values (11.23-20.50 µg/mL) obtained after 24 h of exposure revealed that the oils were notably toxic. The oil obtained from shoots gathered in September during the seed-ripening stage and containing appreciable amounts of palustrol (26.0 ± 2.5%), ledol (21.5 ± 4.0%), and ascaridol (7.0 ± 2.4%) showed the highest toxic activity. Radical scavenging activity of Rh. tomentosum EOs depended on the plant vegetation stage. The highest activities were obtained for EOs isolated from young shoots collected in June (48.19 ± 0.1 and 19.89 ± 0.3 mmol/L TROLOX (6-hydroxy-2,5,7,8-tetra-methylchromane-2-carboxylic acid) equivalent obtained by, respectively, ABTS•+ (2,2'-amino-bis(ethylbenzothiazoline-6-sulfonic acid) diammonium salt) and DPPH•(2,2-diphenyl-1-picrylhydrazyl) assays). Agar disc diffusion assay against pathogenic yeast Candida parapsilosis revealed the potential antifungal activity of EOs. An alternative investigation of antifungal activity employed mediated amperometry at yeast Saccharomyces cerevisiae-modified electrodes. The subjection of yeast cells to vapors of EO resulted in a three to four-fold increase of electrode responses due to the disruption of yeast cell membranes.

Composition, Seasonal Variation, and Biological Activities of Lantana camara Essential Oils from Côte d'Ivoire.

This work aims to study the variations in the composition of Lantana camara leaf, flower, and stem essential oils over two years. L. camara organs were harvested in Bregbo (East Côte d'Ivoire) each month from June 2015 to June 2017. The essential oils were obtained by hydrodistillation and characterized by GC-MS and 13C NMR. Eighty-four compounds accounting for 84.4-99.1% of the essential oils have been identified. The essential oils hydrodistillated from L. camara are dominated by sesquiterpenes such as (E)-ß-caryophyllene and α-humulene, which were found in all samples. Some monoterpenes such as thymol, sabinene, and α-pinene were also present. Statistical analysis (principal component analysis and clustering) revealed a high variability in essential oil composition between the different organs and also within the studied periods, as the thymol proportion was higher during flowering and fruiting months. In addition, the stem, flower, and fruit essential oils were more concentrated in thymol than the leaf essential oils. The proportions of (E)-ß-caryophyllene and α-humulene were strictly inverted with the thymol proportion throughout the harvest period or vegetative cycle. The antioxidant, anti-inflammatory and insecticidal activities of leaves and flowers essential oils were also studied. Results showed that L. camara leaf and flower essential oils displayed high antioxidant, anti-inflammatory and insecticidal activities.

Identification of the Volatile Components of Galium verum L. and Cruciata leavipes Opiz from the Western Italian Alps.

The chemical composition of the volatile fraction from Galium verum L. (leaves and flowers) and Cruciata laevipes Opiz (whole plant), Rubiaceae, was investigated. Samples from these two plant species were collected at full bloom in Val di Susa (Western Alps, Turin, Italy), distilled in a Clevenger-type apparatus, and analyzed by GC/FID and GC/MS. A total of more than 70 compounds were identified, making up 92%-98% of the total oil. Chemical investigation of their essential oils indicated a quite different composition between G. verum and C. laevipes, both in terms of the major constituents and the dominant chemical classes of the specialized metabolites. The most abundant compounds identified in the essential oils from G. verum were 2-methylbenzaldheyde (26.27%, corresponding to 11.59 µg/g of fresh plant material) in the leaves and germacrene D (27.70%; 61.63 µg/g) in the flowers. C. laevipes essential oils were instead characterized by two sesquiterpenes, namely ß-caryophyllene (19.90%; 15.68 µg/g) and trans-muurola-4(15),5-diene (7.60%; 5.99 µg/g); two phenylpropanoids, benzyl alcohol (8.30%; 6.71 µg/g), and phenylacetaldehyde (7.74%; 6.26 µg/g); and the green-leaf alcohol cis-3-hexen-1-ol (9.69%; 7.84 µg/g). The ecological significance of the presence of such compounds is discussed.

Evaluation of Phytochemical Compositions and Biological Properties of Achillea gypsicola at Different Phenological Stages.

Phytochemicals, which are commonly found at different levels in many medicinal plants, are natural strong antioxidants used in traditional medicine. In this research, determination of differences of phytochemical compositions and biological properties were aimed as periodically (pre-, full and post flowering) and daily (6 am, 1 pm and 8 pm) in Achillea gypsicola Hub.-Mor. The volatile oils belonging to A. gypsicola were obtained by hydrodistillation and analyzed by gas chromatography-flame ionization detection (GC-FID) and gas chromatography-mass spectrometry (GC/MS). The antimicrobial activities of the volatile oils were determined with disc diffusion method. The microdilution method was used to determine minimum inhibitory concentration (MIC). Total phenolic and flavonoid contents were determined by spectrophotometric methods and antioxidant capacities were evaluated by 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical, reducing power (RP) and metal chelating activity (MCA) assay. In addition, the phenolic acid and flavonoid compositions were evaluated by reversed phase-high-performance liquid chromatography (RP-HPLC). This study presented a comprehensive report for the first time on evaluation of the phytochemical composition and the biological properties of A. gypsicola at different phenological stages. Thirty-two compounds, containing the major component as camphor, 1,8-cineole and borneol, were detected. Designated harvest time for the highest yield of volatile oils was found to be at full flowering stage-1 pm. It has been observed that the volatile oil composition changes periodically and even daily. Also, in this research, menthol and menthone were found as the composition of volatile oil in Achillea species for the first time. Full flowering stage was found as the richest period in terms of phenolic acid and flavonoid compositions of A. gypsicola for the first time. The species examined in this research showed a high antioxidant and antimicrobial activity in comparison to other studies with Achillea species. The volatile oils exhibited high performances with range of inhibition zones (8.3-42.3 mm) and minimum inhibitory concentration values (2.25-144 µg/ml). Besides, a high correlation between antioxidant activity and phenolic content of A. gypsicola was found. These results suggest that A. gypsicola can be used as a safe source in the cosmetic, food and pharmaceutical industries.