Essential oils of Phlomis leucophracta,Phlomis chimerae and Phlomis grandiflora var. grandiflora from Turkey

The essential oils of three species of Phlomis from Turkey, Phlomis leucophracta, Phlomis chimerae and Phlomis grandiflora var. grandiflora have been studied. The main constituents of P. leucophracta essential oil were β-caryophyllene (20.2%), α-pinene (19.2%) and limonene (11.0%). This species also contained three diterpene derivatives, 15-isopimaradiene, manoyl oxide and epi-13-manoyl oxide that summed 1.4%. In P. chimerae the principal compounds were β-caryophyllene (31.6%), α-pinene (11.0%), germacrene D (6.1%), limonene (5.5%) and linalool (4.7%). In P. grandiflora var. grandiflora, germacrene D (45.4%), β-caryophyllene (22.8%) and bicyclogermacrene (4.9%) were among the principal derivatives.     

Survival in different habitats: Extreme ultramafic and calcareous soils affect Stachys recta essential oils composition

Two populations of Stachys recta growing in Italy on ultramafic and calcareous soils have been studied for their essential oils. Although the yields were comparable, the composition of the essential oils differed significantly. Plants growing on ultramafic soil produced mainly non-terpene derivatives (55.7%), of which the most abundant ones were 1-octen-3-ol (38.2%) and (E)-3-hexen-1-ol (5.9%); the terpenes α-cadinol (6.1%) and δ-cadinene (5.6%) were also significantly represented. In contrast, the populations living on calcareous soil produced an essential oil dominated by terpenes (93.8%), with germacrene D (18.8%), β-caryophyllene (17.7%), 1,8-cineole (15.9%) and α-pinene (14.2%) among the main components.     

Variability in essential oil composition of Piper dilatatum L.C. Rich

Twelve samples of air-dried aerial parts of Piper dilatatum L. C. Rich yielded essential oils and their volatile constituents were analyzed by GC and GC–MS. Sesquiterpenes, both hydrocarbons and oxygenated, were the most highly represented classes, the former ranging from 31.5% to 87.7% and the latter varying from 1.8% to 49.4%. Using hierarchical cluster analysis, the oils were divided into seven groups, whose main constituents were: (E)-caryophyllene, α-cadinol and germacrene D (group A); spathulenol, bicyclogermacrene and (Z)-β-ocimene, (group B); spathulenol, germacrene D and (E)-nerolidol, (group C); germacrene D, limonene, α-phellandrene and bicyclogermacrene (group D); β-elemene, germacrene D and β-pinene (group E); curzerene, p-cymene and α-eudesmol (group F); and (Z)-α-bisabolene, curzerene and germacrene D (group G). We have seen that Piper oils from the Amazon present as major constituents terpenoids and phenylpropanoids, always with the predominance of one over another. The essential oils of P. dilatatum presented in this paper, containing only mono- and sesquiterpenes as its major components, is further chemotaxonomic evidence of this dichotomy in the Piper genus.     

GC-MS analysis of the essential oils of Juniperus communis L. berries growing wild in the Molise region: Seasonal variability and in vitro antifungal activity

Juniperus communis L., also known as the common juniper, is a dioecious aromatic evergreen shrub and has been traditionally used in many countries as a diuretic, antiseptic, and digestive and as a flavor to aromatize certain alcoholic beverages. We analyzed the chemical variability in the volatile profiles from berries of J. communis, harvested in one of the oldest European parks, the National Park of Abruzzo, Lazio, and Molise (PNALM, Central Italy). We examined the berries in different phases of the biological cycle for 1 year (at six ripening stages). Hydrodistilled essential oils from the fresh berries were analyzed by gas chromatography–flame ionization detection (GC-FID), gas chromatography–mass spectrometry (GC-MS) and principal component analysis (PCA). A total of 90 components were detected, and remarkable qualitative and quantitative differences were observed in the chemical components during the ripening stages, from the green unripe berries to the bluish-black berries harvested at full maturity. The essential oils were an α-pinene (13.43–32.34%) chemotype. The monoterpene hydrocarbons decreased during the ripening with a progressive increase in sesquiterpenes such as germacrene D (12.29–17.59%) and β-caryophyllene (7.71–8.51%), which are the major components in ripe berry essential oils. The sesquiterpene hydrocarbon fraction (65.3–47.9%) also contained α-humulene, germacrene B, δ-cadinene, bicyclogermacrene, and eudesma 4(14),11 diene. Germacrene D and β-caryophyllene in high concentrations may be considered as marker components of the genus Juniperus from the Molise region. This particular chemical composition has been reported for the first time. It is interesting to note the presence of β-caryophyllene (7–11%), whose inhalation has been reported to affect anxiety and depression in a rat model. An in vitro antifungal assay showed that the essential oil from green and ripe berries inhibits the growth of Sclerotium rolfsii, a phytopathogen fungus that causes post-harvest diseases in many fruits and vegetables.     

Essential oil composition of four Lomatium Raf. species and their chemotaxonomy

The composition of the essential oils of Lomatium dasycarpum ssp. dasycarpum, Lomatium lucidum, Lomatium macrocarpum var. macrocarpum and Lomatium utriculatum is described. Identification of components was determined from their GC, GC/MS data and many were confirmed by coinjections with authentic samples. Several components were isolated by liquid and gas chromatographic techniques and their structures confirmed from their ¹H and ¹³C NMR spectral data. 2-Methyl and 3-methylbutanoates were the major components of L. dasycarpum fruits as well as stems and leaves oils. β-Phellandrene/limonene, decanal, dodecanal, bornyl acetate, germacrene D, α-humulene and bicyclogermacrene were the major components of the corresponding L. lucidum oils. α-Pinene and β-pinene were the major components of the fruit oil of L. macrocarpum. Its stem and leaf oil was rich in peucenin 7-methyl ether, β-caryophyllene, (Z)-3-hexenol, palmitic acid, linoleic acid and (E)-2-hexenal. Sabinene, (Z)-ligustilide, terpinen-4-ol, β-phellandrene/limonene, β-caryophyllene, myrcene, α-pinene and β-pinene were the major compounds in L. utriculatum fruit oil, while its stem and leaf oil was rich in (Z)-ligustilide, palmitic acid, terpinen-4-ol, linoleic acid and germacrene D. (Z)-Falcarinol was a major component of all the four root oils.     

The composition and antibacterial activity of essential oils in three Ocimum species growing in Romania

In this study the glandular hair morphology, chemical composition and antimicrobial activity of the essential oils from three Ocimum species have been investigated (Ocimum basilicum L. var. Genovese, O. gratissimum and O. tenuiflorum). The indumentum shows little variation among the investigated species with both glandular and non-glandular hairs presents. Glandular hairs on the three species are peltate and capitate (with various cell numbers in the stalk and gland). The samples of essential oils obtained from the plant aerial organs by hydrodistillation have been analyzed by GC-MS. Linalool (65.38%, 74.22%, 38.60%), eugenol (5.26%, 3.47%, 10.20%) and tau-cadinol (8.18%, 3.47%, 10.20%) appear as the main components in Ocimum basilicum L. var. Genovese, O. gratissimum and O. tenuiflorum. The oils also contain lower levels of α-bergamotene, 1,8-cineole, germacrene D, β-ocimene, α-caryophyllene, camphor, and α-guaiene. All essential oils showed antibacterial activity against Staphylococcus aureus and Escherichia coli depending on their concentration. Ocimum basilicum L. var. Genovese oil produced the strongest antibacterial effect on S. aureus and E. coli.     

Volatiles from Marina neglecta: Biocide effect on insect vectors of tropical diseases in Southern Mexico

Preventive measures based in the control of insect vectors are considered as the best choice to decrease the incidence of insect-borne diseases. Herein we report on the volatile content of the leaf essential oils from Marina neglecta, a medicinal plant distributed in the tropical regions of southern Mexico. In order to investigate the chemical variation of the essential oils, a volatile screening was performed during the four seasons of the years 2016–2019. Simultaneously, their biological activity was tested on distinct life stages of Meccus pallidipennis, M. bassolsae, Aedes aegypti and A. albopictus. Essential oils were mainly constituted of β-pinene (>30%) β-caryophyllene (>25%) and germacrene D (>13%). Dorsal-abdomen application of essential oils on triatomines, revealed an efficient LC₅₀ for nymphs of the stages I to III (4 µg/insect), nymphs of the stages IV to V (5–6 µg/insect), and adults (7–8 µg/insect). The LT₅₀ for the stages I to III was between 6 and 8 h, whereas that for the stages IV to V and adults oscillated between 12 and 16 h and 22 to 26 h, respectively. Fumigation experiments performed on nymph V, demonstrated that 300 µg L^?1 air produced 100% mortality after 72 h post-treatment. Among tested volatiles, β-pinene and β-caryophyllene produced a comparable mortality rate (p < 0.01) than that of essential oils in the stages assayed. Essential oils showed strong larvicidal (LC₅₀, 24–36 µg mL^?1) and adulticidal (35–48 µg mL^?1) activities in mosquito species with an LT₅₀ of 4.5 h and 25–35 min, respectively. The evaluation of β-pinene produced a significant mortality rate (p < 0.01) in larvae whereas germacrene D was the most effective volatile (p < 0.01) against adults of both mosquito species. According to our results, β-pinene was the most effective volatile against the four insect species evaluated and its effect was comparable to that of the essential oil.     

Essential Oil Variability in Natural Populations of Artemisia campestris (L.) and Artemisia herba‐alba (Asso) and Incidence on Antiacetylcholinesterase and Antioxidant Activities

The intraspecific variability of Artemisia herba‐alba and A. campestris essential oils and the evaluation of their antioxidant and antiacetylcholinesterase activities were determined. Artemisia herba‐alba essential oil was found rich in camphor (19.61%), α‐thujone (19.40%), β‐thujone (9.44%), chrysanthenone (9.26%), and trans‐sabinyl acetate (8.43%). The major compounds of A. campestris essential oil were germacrene D (16.38%), β‐pinene (16.33%), and limonene (9.17%). Significant variation in the essential oil composition was observed among populations of each species. The divergence between populations was attributed to the variation of some climatic factors such as altitude, annual rainfall, winter cold stress, summer precipitation, summer drought stress, evapotranspiration, and humidity. Artemisia herba‐alba and A. campestris essential oils exhibited promising antioxidant and antiacetylcholinesterase activities. The level of activity varied significantly according to the species and the essential oil. The highest scavenging activity (IC₅₀ = 0.14 mg/ml) and the uppermost capacity to prevent β‐carotene bleaching (IC₅₀ = 0.10 mg/ml) characterized A. campestris from population 6. A. campestris population 3 possessed the uppermost ability to reduce ferric ions (450.7 μmol Fe²⁺/g EO). The population 2 of A. campestris showed the strongest antiacetylcholinesterase activity (IC₅₀ = 0.02 mg/ml). The variation of these activities between the essential oils was explained by their composition differences.     

Chemical composition and antimicrobial activity of the essential oil of endemic Dalmatian black pine (Pinus nigra ssp. dalmatica)

The chemical composition and the antimicrobial activity of the essential oil isolated from the needles of endemic Dalmatian black pine (Pinus nigra ssp. dalmatica) from Croatia were investigated. The chemical composition of the essential oil was determined by GC and GC/MS analyses, and the main compounds identified were α-pinene, β-pinene, germacrene D, and β-caryophyllene. Disc-diffusion and broth-microdilution assays were used for the in vitro antimicrobial screening. The Dalmatian black pine essential oil exhibited a great potential of antibacterial activity against Gram-positive bacteria (MIC=0.03-0.50% (v/v)) and a less pronounced activity against Gram-negative bacteria (MIC=0.12-3.2% (v/v)). The volatile compounds also inhibited the growth of all fungi tested, including yeast.     

Application of multidimensional gas chromatography to the enantioselective characterisation of the essential oil of Eupatorium buniifolium Hooker et Arnott

The qualitative and quantitative composition of the essential oil from aerial parts of Eupatorium buniifolium Hooker et Arnott (Asteraceae) has been investigated for the first time. The essential oils were obtained by steam distillation of leaves and analysed by GC-MS; 44 components were identified. Monoterpene and sesquiterpene hydrocarbons, especially alpha-pinene (14.7%), beta-elemene (12.2%), germacrene D (11.5%), trans-beta-guaiene (6.5%) and (E)-caryophyllene (4.3%), were the major constituents found in the oils. The characterisation of E. buniifolium by enantioselective GC was performed by evaluation of the enantiomeric ratios of alpha-pinene, sabinene, beta-pinene, limonene, terpinen-4-ol and germacrene D.     

Variation in essential oil composition of Leonotis leonurus,an important medicinal plant in South Africa

Leonotis leonurus widely used by traditional healers in southern Africa for treatment of various ailments, is well known for its reported psychoactive properties. The present study was undertaken to investigate the variation in essential oil composition between geographically distinct populations of L. leonurus in South Africa using gas chromatography. Plant material (n = 50) was collected from three provinces of South Africa. Essential oils of the aerial parts were obtained by hydrodistillation and analysed using one and two dimensional gas chromatography. Twenty-six compounds accounted for more than 80% of the total composition of the oil. Eight major constituents in the oil, representing about 50% of the total oil composition, were identified by both GC–MS–FID and GCxGC–ToF–MS. These major compounds were trans-β-ocimene (0.1–5.0%), cis-β-ocimene (0.1–31.5%), β-caryophyllene (0.3–15.0%), caryophyllene oxide (0.1–5.0%), α-humulene (0.4–18.2%), γ-elemene (0.4–10.6%), α-cubebene (0.2–12.0%) and germacrene D (0.1–22.1%). Marked similarities exist in the essential oil composition between populations; differences are mostly quantitative when determined by GC–MS–FID, while GCxGC–ToF–MS data reveals both quantitative and qualitative differences.Untargeted multivariate analysis was performed using SIMCA-P + 14.0 PCA and OPLS-DA methods, identifying two distinct clusters, inland and coastal populations.     

Genetic structure and essential oil composition in wild populations of Salvia multicaulis Vahl.

The phytochemical study on ten populations of Salvia multicaulis Vahl. revealed that their essential oil qualitative profiles contained a significant amount of monoterpene hydrocarbons, which were the most abundant compounds. Besides, α-Pinene was the major constituent in all studied populations' essential oils. Significant correlations were observed between edaphic parameters and some major essential oil compounds. According to clustering analyses of the chemical data, the S. multicaulis populations were divided into three chemotypes: β-caryophyllene, camphene and camphor, and limonene. The population genetics study showed significant molecular differences among the populations. The Mantel test indicated a significant positive correlation between the geographical distances and genetic diversity, exhibiting a low amount of gene flow and a considerable genetic differentiation value. We also detected four genotypes based on the Nei's genetic distance and structure analysis. The identified chemical and genetic similarities/differences among these populations were correlated with edaphic parameters and geographic distances, suggesting that environmental factors are the primary drivers of the chemical polymorphism of essential oils in S. multicaulis populations.     

Essential oil composition of Achyrocline flaccida (Weinm.) DC. (Asteraceae) from different locations of Argentina

The qualitative and quantitative composition of the essential oils obtained from the inflorescences of Achyrocline flaccida (Asteraceae) has been investigated for the first time. Plant material was collected from eleven locations in Argentina. The essential oils were obtained by hydrodistillation (0.1–0.8% v/w, dried material) and analyzed by GC–FID–MS. Eighty-three compounds were identified representing more than the 90% of the oils. The major components were α-pinene and β-caryophyllene. Statistical analysis was performed in order to evaluate the variability of the essential oils analyzed. Two groups were formed reflecting only quantitative differences in the content of major compounds. The chemical pattern of essential oils observed for A. flaccida is similar to other Achyrocline species studied, except Achyrocline hyperchlora.     

Chemical traits and antimicrobial activity of endemic <Emphasis Type="Italic">Teucrium arduini</Emphasis> L. from Mt Biokovo (Croatia)

Chemical composition of the essential oil (analysed by GC-FID and GC-MS), the content of macroelements and trace elements (analysed by ICP-AES), and antimicrobial activities were investigated in Teucrium arduini L. from Mt Biokovo (Croatia). Additionally, a study on the types and distribution of glandular trichomes which produce essential oils was investigated. The oil was characterized by a high concentration of sesquiterpene hydrocarbons (68.5%) of which β-caryophyllene (32.9%) and germacrene D (16.4%) being the major compounds. Among the macroelements, the content of calcium was the highest (9772 mg/kg), while the content of sodium was the smallest (117.74 mg/kg). Among the micronutrients, the most represented element was iron (72.07 mg/kg). The content of each investigated toxic metal (As, Hg, Pb, Cd and Cr) was below permissible levels. The essential oils showed antimicrobial activity against bacterial species tested, with MIC values ranging from 6.25 mg/mL to 37.50 mg/mL. Fungal species were susceptible with MIC values from 7.81 mg/mL and 25.00 mg/mL.     

Essential oil of Stachys aleurites from Turkey

The essential oil obtained from the aerial parts of the Turkish endemism Stachys aleurites (Lamiaceae) has been studied. The main constituents were sesquiterpene hydrocarbons: β-caryophyllene (33.7%), bicyclogermacrene (14.5%) and germacrene D (9.6%). The main monoterpene was α-pinene (8.4%). Some chemotaxonomical considerations have been provided.     

Chemotaxonomic significance of volatile compounds in Thymus samius and its related species Thymus atticus and Thymus parnassicus

Thymus samius, a rare species endemic to the island of Samos (East Aegean, Greece), has been considered to be of possible hybrid origin, with Thymus cilicicus, Thymus parnassicus or Thymus zygioides as putative parents. Morphologically it also resembles Thymus atticus. In order to evaluate any possible chemotaxonomic relationships indicated by the qualitative and/or quantitative differentiation of volatile compounds, the essential oils of T. samius, T. parnassicus and T. atticus were analyzed and the oils of T. cilicicus and T. zygioides were used for comparison. T. atticus presents considerable variation in chemical constituents, with all Greek populations being poor in thymol/carvacrol and rich in (E)-nerolidol, germacrene D, (E)-caryophyllene, caryophyllene oxide, 1,8-cineole, α-pinene and camphene, depending on the sample. T. parnassicus shows remarkable qualitative stability in its volatile constituents, and all its populations have a similar profile with (E)-caryophyllene being the most prominent compound. T. samius is characterized by the presence of germacrene D and β-bisabolene, which constitute almost half its oil percentage. This species is also characterized by a low amount of monoterpenes; the latter exist in a considerable percentage in the related species. Our results indicate that T. samius does not show similarity or intermediacy in chemical compounds with any given couple of T. atticus, T. parnassicus, T. cilicicus, or T. zygioides.     

Capitula essential oil composition of seven Centaurea species (sect. Acrocentron,Asteraceae) – Taxonomic implication and ecological significance

In this paper, we analyzed the capitula essential oil composition of seven Centaurea species, six of which belong to Centaurea calocephala complex, and the related species Centaurea melanocephala Pančić (subgenus Acrocentron, tribus Cardueae, subtribus Centaureinae) which inhabit Balkans Peninsula. The volatile organic compounds were extracted by simultaneous distillation extraction, using Likens-Nickerson type apparatus and the oils were analyzed by GC-FID and GC-MS. In total, 146 compounds were identified (95.5–99.4% of the total oil composition). The essential oils were dominated by sesquiterpenes (39.1–81.7%). The most abundant components were β-caryophyllene (3.1–28.3%), caryophyllene oxide (4.7–31.2%), germacrene D (2.9–22.2%), followed by n-hexacosane, [2Z,6E]-farnesol, eudesma-4(15),7-dien-1-β-ol, α-cadinole, germacrene B, trans-verbenol, and hexanal that were present in some samples in relatively high abundances. The geographic region and the color of capitula were analyzed in correlation with essential oil composition. Also, all investigated species are characterized by the different amount of most dominant components, which leads to the hypothesis that they “choose” different strategies: different combination and amounts of attractants for pollinators. Ecological correlations and taxonomical implications are further discussed.     

Chemical Composition and Cytotoxic Evaluation of the Essential Oil of Phyllogonium viride (Phyllogoniaceae,Bryophyta)

The present study aimed to determine the chemical composition and biological activity of the essential oil obtained from Phyllogonium viride Brid. (Phyllogoniaceae, Bryophyta), whose samples were collected in southern Brazil. For the first time, the cytotoxic activity of the essential oil of P. viride in breast and colorectal tumor cells (MCF-7 and HCT-116) was evaluated, as well as the cytotoxic potential of this oil in non-tumoral cells of human immortalized keratinocytes (HaCaT) via MTT assay. The compounds majorly found in P. viride essential oil were β-bazzanene (20.30 %), β-caryophyllene (17.06 %), β-chamigrene (14.02), and germacrene B (11.72 %). Treatment with P. viride essential oil in the different tested cell lines did not induce any toxicity in most of the tested concentrations. These data contribute to generating new scientific information about this understudied plant species. Furthermore, the chemical characterization of the compounds present in the essential oil of P. viride can lead to greater elucidation of its biotechnological potential.     

Antioxidant and Antibacterial Activities of Crude Extracts and Essential Oils of Syzygium cumini Leaves

This research highlights the chemical composition, antioxidant and antibacterial activities of essential oils and various crude extracts (using methanol and methylene chloride) from Syzygium cumini leaves. Essential oils were analyzed by gas chromatography-mass spectrometry (GC-MS).The abundant constituents of the oils were: α-pinene (32.32%), β-pinene (12.44%), trans-caryophyllene (11.19%), 1, 3, 6-octatriene (8.41%), delta-3-carene (5.55%), α-caryophyllene (4.36%), and α-limonene (3.42%).The antioxidant activities of all extracts were examined using two complementary methods, namely diphenylpicrylhydrazyl (DPPH) and ferric reducing power (FRAP). In both methods, the methanol extract exhibited a higher activity than methylene chloride and essential oil extracts. A higher content of both total phenolics and flavonoids were found in the methanolic extract compared with other extracts. Furthermore, the methanol extract had higher antibacterial activity compared to methylene chloride and the essential oil extracts. Due to their antioxidant and antibacterial properties, the leaf extracts from S. cumini may be used as natural preservative ingredients in food and/or pharmaceutical industries.     

The essential oil of Origanum vulgare L. ssp. vulgare growing wild in vilnius district (Lithuania)

The plants of wild Origanum vulgare L. ssp. vulgare were collected in 10 localities of Vilnius district (Lithuania) in 1995-1999. The main constituents of the essential oils from 8 localities were beta-ocimene (14.9-21.6%), germacrene D (10.0-16.2), beta-caryophyllene (10.8- 15.7%) and sabinene (6.6- 4.2%). The essential oils from two localities contained only three above compounds as major components: germacrene D, beta-ocimene and sabinene or beta-caryophyllene, beta-ocimene and germacrene D. Three chemotypes of essential oils were identified. The main chemotype was beta-ocimene germacrene D-beta-caryophyllene. The terpenic hydrocarbons made up 52.8-80.6% of the essential oils. The 42 identified components made up 85.6-98.0% of the essential oil.