Cytotoxic Essential Oils from Eryngium campestre and Eryngium amethystinum (Apiaceae) Growing in Central Italy

Eryngium campestre and E. amethystinum are thorny herbs belonging to the Apiaceae family and spontaneously growing in stony pastures and dry meadows, preferentially on calcareous substrates. In the Mediterranean countries, these plants have been used as a food or traditional remedies to treat various ailments. In the present work, we have analyzed the chemical composition of the essential oils distilled from the aerial parts by GC‐FID and GC/MS, and evaluated their cytotoxic effects on a panel of human cancer cells, namely A375 (human malignant melanoma), MDA‐MB 231 cells (human breast adenocarcinoma), and HCT116 cells (human colon carcinoma), by the MTT assay. Furthermore, the Eryngium essential oils were evaluated for antioxidant and acetylcholinesterase (AChE) activities. The two essential oils were rich in sesquiterpene hydrocarbons, with germacrene D as the major compound, accompanied by allo‐aromadendrene, β‐elemene, spathulenol, and ledol. They turned out to be highly cytotoxic on the tumor cells, with IC₅₀ values (1.65 – 5.32 and 1.57 – 2.99 μg/ml for E. amethystinum and E. campestre, respectively) comparable or close to those of the anticancer drug cisplatin. The E. amethystinum essential oil exhibited a moderate antioxidant activity, whereas that of E. campestre a weak AChE inhibition.     

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

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

Chemical Composition and Biological Investigations of Eryngium triquetrum Essential Oil from Algeria

The chemical composition, antibacterial and antioxidant activities of the essential oil obtained from Eryngium triquetrum from Algeria were studied. The chemical composition of sample oils from 25 locations was investigated using GC‐FID and GC/MS. Twenty‐four components representing always more than 87% were identified in essential oils from total aerial parts of plants, stems, flowers and roots. Falcarinol is highly dominant in the essential oil from the roots (95.5%). The relative abundance of falcarinol in the aerial parts correlates with the phenological stages of the plant. Aerial parts of E. triquetrum produce an essential oil dominated by falcarinol during the early flowering stage, and then there is a decrease in falcarinol and rebalancing of octanal during the flowering stage. To our knowledge, the present study is the first report of the chemical composition of E. triquetrum essential oil. Evaluation of the antibacterial activity by means of the paper disc diffusion method and minimum inhibitory concentration assays, showed a moderate efficiency of E. triquetrum essential oil. Using the DPPH method, the interesting antioxidant activity of E. triquetrum essential oil was established. These activities could be attributed to the dominance of falcarinol. The outcome of our literature search on the occurrence of falcarinol in essential oils suggests that E. triquetrum from Algeria could be considered as a possible source of natural falcarinol.     

Chemical Composition and Antimicrobial Activity of the Essential Oil from Aerial Parts and Roots of Eryngium barrelieri Boiss. and Eryngium glomeratum Lam. from Tunisia

The study of chemical composition and biological activity of unexplored essential oils may open new perspectives on their potential use in facing major health concerns such as drug‐resistant infections. The present study investigates the chemical composition and antimicrobial effects of previously unstudied essential oils obtained from genus Eryngium: Eryngium glomeratum Lam . and Eryngium barrelieri Boiss . The chemical compositions of the essential oils from aerial parts and roots of both species were studied using GC and GC/MS analytical technics. The analysis led to the identification of 102 compounds totalizing 85 – 94% of all detected compounds. Essential oils were characterized by the predominance of oxygenated sesquiterpenes. The oils obtained from aerial parts were tested against 36 microbial strains by agar dilution method and showed minimum inhibitory concentrations (MIC) in the range of 2 – 625 μg/ml. A strong antibacterial activity against multiresistant Pseudomonas aeruginosa was observed especially from E. glomeratum essential oil with MIC value up to 2 μg/ml. These findings give significant information about the pharmacological activity of these essential oils, which suggest their potential use to develop new remedies, or as sources of active compounds.     

Chemical Composition and Antimicrobial Activity of the Essential Oil of Juniperus excelsa M.Bieb. Growing Wild in Lebanon

The essential oils (EOs) isolated from the leaves and twigs of Juniperus excelsa M.Bieb . growing wild in Lebanon were characterized, and their antimicrobial activity and antiradical capacity were evaluated. The EOs were obtained by hydrodistillation using a Clevenger‐type apparatus and characterized by GC and GC/MS analyses. The antimicrobial activity was evaluated by determining minimal inhibitory concentrations (MICs) against a Gram‐positive and a Gram‐negative bacterium, a yeast, and a dermatophyte with the broth microdilution technique. A total of 28 constituents was identified and accounted for 90.1 and 95.6% of the twig and leaf EO composition, respectively. Both EOs were essentially composed of monoterpene hydrocarbons (46.7 and 59.6% for twig and leaf EOs, resp.) and sesquiterpenes (39.4 and 32.1%, resp.). The main components were α‐pinene, α‐cedrol, and δ‐car‐3‐ene. The J. excelsa EOs did not show any antiradical potential, but revealed interesting in vitro antimicrobial activities against Staphylococcus aureus and Trichophyton rubrum (MICs of 64 and 128 μg/ml, resp.). The three major compounds were tested separately and in combination according to their respective amounts in the oil. δ‐Car‐3‐ene was the most active component and is undoubtedly one of the constituents driving the antifungal activity of J. excelsa essential oil, even though synergies are probably involved.     

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

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

Composition and Activity against Oral Pathogens of the Essential Oil of Melampodium divaricatum (Rich.) DC.

The chemical composition of the essential oil isolated from the aerial parts of Melampodium divaricatum (Rich .) DC. (Asteraceae) was characterized by GC‐FID and GC/MS analyses. (E)‐Caryophyllene (56.0%), germacrene D (12.7%), and bicyclogermacrene (9.2%) were identified as the major oil components. The antimicrobial activity of the oil against seven standard strains of oral pathogens from the American Type Culture Collection (ATCC) was evaluated by determining minimum inhibitory concentrations (MICs) using the microdilution method. MIC Values below 100 μg/ml were obtained against Streptococcus sobrinus (90 μg/ml), Lactobacillus casei (30 μg/ml), S. mutans (20 μg/ml), and S. mitis (18 μg/ml). In contrast, the MIC values of the major oil compound (E)‐caryophyllene were higher than 400 μg/ml against all pathogens, suggesting that the activity of the oil might depend on minor oil components and/or on synergistic effects. The M. divaricatum essential oil is a promising agent to include in anticariogenic oral rinse formulations for the control of oral pathogens.     

Phytochemical constituents and inhibitory activity towards methicillin-resistant Staphylococcus aureus strains of Eryngium species (Apiaceae)

The chemical composition of the essential oils of Eryngium campestre, E. thorifolium, and E. creticum (Apiaceae), growing in the Aegean region of Turkey (Mount Sandras, Denizli), was determined by direct thermal desorption (DTD)-GC/MS analyses. A total of 49 components were identified in the oils, α-pinene and hexanal being the major compounds. The three essential oils were also tested for their inhibitory activity of nine different methicillin-resistant Staphylococcus aureus (MRSA) strains by the agar disc diffusion method. The anti-MRSA activity of E. thorifolium oil, the most active of the three oils, was comparable with those of the reference antibiotic vancomycin and oregano oil, although somewhat lower.     

Chemical Composition of Essential Oils of Xanthium spinosum L., an Invasive Species of Corsica

Xanthium spinosum L. is a highly invasive plant originated from South America throughout the world as well as in Corsica Island. The chemical composition of X. spinosum essential oils from 25 Corsican locations was investigated using GC‐FID and GC/MS. Seventy‐four components, which accounted for 96.2% of the total amount, were reported for the first time in the essential oil from aerial parts. The main compounds were eudesma‐4(14),7‐dien‐1β‐ol ( 61 ; 21.3%), germacrene D ( 36 ; 8.8%) and cadalene ( 60 ; 8.7%). Comparison with the literature highlighted the originality of the Corsican essential oil and eudesma‐4(14),7‐dien‐1β‐ol could be used as taxonomical marker to the systematics of the Xanthium genus. The essential oils obtained from separate organs and during the plant vegetative cycle were also studied to gain more knowledge about the correlations between the volatile production and the phenological states of this weed. The production of oxygenated sesquiterpenes was predominant during the plant‐flowering process. The study focuses on direct correlation between the chemical composition of individual 25 oil samples and the morphological differences of the plant. Our results have gained more knowledge about the secondary metabolite production that occurs during the plant life, they could be interesting in order to manage the dispersal of X. spinosum.     

Volatile‐Oils Composition,and Bioactivity of the Essential Oils of Plectranthus barbatus,P. neochilus,and P. ornatus Grown in Portugal

Volatile‐oils chemical composition and bioactivity of the essentail oils from Plectranthus barbatus, P. neochilus, and P. ornatus (Lamiaceae) were assessed. Aerial parts from these three related Plectranthus species were collected from cultivated plants grown in Portugal, during vegetative and flowering phases. Volatiles, isolated by distillation? extraction, were analyzed by GC and GC/MS. Monoterpene hydrocarbons (12–74%) and sesquiterpene hydrocarbons (4–45%) constituted the main fractions in all volatiles. α‐Pinene ( 3 ; 12–67%), oct‐1‐en‐3‐ol ( 6 ; traces–28%), β‐pinene ( 7 ; 0.1–22%), and β‐caryophyllene ( 50 ; 7–12%) dominated P. barbatus volatiles. P. neochilus major volatile components were α‐terpenyl acetate ( 41 ; traces–48%), α‐thujone ( 2 ; 2–28%), β‐caryophyllene ( 50 ; 2–28%), β‐pinene ( 7 ; 1–25%), and α‐pinene ( 3 ; 1–19%). Oct‐1‐en‐3‐ol ( 6 ; 13–31%), β‐pinene ( 7 ; 11–24%), α‐pinene ( 3 ; 11–19%), and β‐caryophyllene ( 50 ; traces–11%) were the main constituents from P. ornatus volatiles. These chemical compositions were rather different from those previously found for specimens harvested in Africa and Brazil. Moreover, the volatiles from the flowers are herewith reported for the first time. Essential oils, isolated by hydrodistillation from leaves and stems, showed a yellowish color and unpleasant odor, with yields ranging from 0.08% to 0.84% (v/dry weight). Antioxidant and antimicrobial activities of the essential oils were evaluated by DPPH^. and TBARS assays, and agar disc‐diffusion method, respectively. Results showed low or moderate antioxidant capacity and significant antimicrobial activity against Gram‐positive bacteria.     

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 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 Biological Activity of Abies alba and A. koreana Seed and Cone Essential Oils and Characterization of Their Seed Hydrolates

The chemical composition, including the enantiomeric excess of the main terpenes, the antimicrobial and antiradical activities, as well as the cytotoxicity of Abies alba and A. koreana seed and cone essential oils were investigated. Additionally, their seed hydrolates were characterized. In the examined oils and hydrolates, a total of 174 compounds were identified, which comprised 95.6–99.9% of the volatiles. The essential oils were mainly composed of monoterpene hydrocarbons, whereas the composition of the hydrolates, differing from the seed oils of the corresponding fir species, consisted mainly of oxygenated derivatives of sesquiterpenes. The seed and cone essential oils of both firs exhibited DPPH‐radical‐scavenging properties and low antibacterial activity against the bacterial strains tested. Moreover, they evoked only low cytotoxicity towards normal fibroblasts and the two cancer cell lines MCF‐7 and MDA‐MBA‐231. At concentrations up to 50 μg/ml, all essential oils were safe in relation to normal fibroblasts. Although they induced cytotoxicity towards the cancer cells at concentrations slightly lower than those required for the inhibition of fibroblast proliferation, their influence on cancer cells was weak, with IC₅₀ values similar to those observed towards normal fibroblasts.     

Essential oils from neotropical Myrtaceae: chemical diversity and biological properties

Myrtaceae family (121 genera, 3800-5800 spp.) is one of the most important families in tropical forests. They are aromatic trees or shrubs, which frequently produce edible fruits. In the neotropics, ca. 1000 species were found. Several members of this family are used in folk medicine, mainly as an antidiarrheal, antimicrobial, antioxidant, cleanser, antirheumatic, and anti-inflammatory agent and to decrease the blood cholesterol. In addition, some fruits are eaten fresh or used to make juices, liqueurs, and sweets very much appreciated by people. The flavor composition of some fruits belonging to the Myrtaceae family has been extensively studied due to their pleasant and intense aromas. Most of the essential oils of neotropical Myrtaceae analyzed so far are characterized by predominance of sesquiterpenes, some with important biological properties. In the present work, chemical and pharmacological studies carried out on neotropical Myrtaceae species are reviewed, based on original articles published since 1980. The uses in folk medicine and chemotaxonomic importance of secondary metabolites are also briefly discussed.     

Chemical Composition and Antimicrobial Activity of Essential Oils from Chromolaena laevigata during Flowering and Fruiting Stages

The chemical compositions and antimicrobial activities of essential oils from the leaves, stems, capitula, and cypselas of Chromolaena laevigata were evaluated at two different phenological stages, flowering and fruiting. Thirty‐eight compounds were identified in the crude oils by GC/MS. The sesquiterpene laevigatin was the major constituent of the leaf, capitulum, and cypsela oils, while the sesquiterpene spathulenol was the main component in the stem oils. The antimicrobial activities of the oils were evaluated against Candida albicans, Staphylococcus aureus, Pseudomonas aeruginosa, and Escherichia coli. Stem oil obtained from Chromolaena laevigata during the fruiting stage generally showed the highest activity with minimum inhibitory concentration (MIC) values of 62.5 μg/ml against Candida albicans and S. aureus, and 500 μg/ml against P. aeruginosa and E. coli. Pure laevigatin exhibited MIC values of 500 and 125 μg/ml against C. albicans and S. aureus, respectively, indicating that this constituent could be responsible, at least in part, for the antimicrobial activities detected in the crude oils. More studies concerning the biological activities of isolated derivatives are required to improve our knowledge of the antimicrobial potential of volatile compounds present in native plants.     

Chemical Composition and Antimicrobial Activity of the Essential Oils from New Caledonian Citrus macroptera and Citrus hystrix

The essential oils from the leaves of Citrus macroptera and C. hystrix, collected in New Caledonia, have been analyzed by gas chromatography/mass spectrometry (GC/MS) and evaluated for their antimicrobial activity. A total of 35 and 38 constituents were identified, representing 99.1 and 89.0% of the essential oils, respectively. Both essential oils were rich in monoterpenes (96.1 and 87.0%, resp.), with β‐pinene as major component (33.3 and 10.9%, resp.), and poor in limonene (2.4 and 4.7%, resp.). Other main components of C. macroptera oil were α‐pinene (25.3%), p‐cimene (17.6%), (E)‐β‐ocimene (6.7%), and sabinene (4.8%). The essential oil of C. hystrix was characterized by high contents of terpinen‐4‐ol (13.0%), α‐terpineol (7.6%), 1,8‐cineole (6.4%), and citronellol (6.0%). The antimicrobial activity was evaluated against five bacteria and five fungi strains. Both oils were inactive against bacteria. However, the C. macroptera leaf oil exhibited a pronounced activity against Trichophyton mentagrophytes var. interdigitale, with a minimal‐inhibitory concentration (MIC) of 12.5 μg/ml.     

Chemical Composition and Antimicrobial Activity of the Essential Oil of Ruta chalepensis L. Growing Wild in Lebanon

The essential oils (EOs) isolated from the fresh aerial parts of Ruta chalepensis L. collected in North Lebanon were obtained by solvent‐free microwave extraction (Milestone®), yielding 0.12% EO from both the leaves and a mixture of stems and leaves. The EOs were characterized by GC/MS analysis, and 27 components were identified, which were primarily ketones (88.0–93.2%). The main components were nonan‐2‐one and undecan‐2‐one. The antimicrobial activity of the EOs against a Gram‐positive and a Gram‐negative bacterium, a yeast, and a dermatophyte was evaluated using the broth‐microdilution technique and expressed as minimal inhibitory concentration (MIC). The EOs revealed moderate in vitro antifungal activity against Trichophyton rubrum and Candida albicans.     

Composition and Chemical Variability of Ivoirian Polyalthia oliveri Leaf Oil

The chemical composition of 45 essential oil samples isolated from the leaves of Polyalthia oliveri harvested in three Ivoirian forests was investigated by GC‐FID (retention indices measured on two columns of different polarities), and by ¹³C‐NMR, following a method developed in our laboratory. In total, 41 components were identified. The content of the main components varied drastically from sample to sample: (E)‐β‐caryophyllene (1.2 – 50.8%), α‐humulene (0.6 – 47.7%), isoguaiene (0 – 27.9%), alloaromadendrene (0 – 24.7%), germacrene B (0 – 18.3%), δ‐cadinene (0.4 – 19.3%), and β‐selinene (0.2 – 18.5%). The analysis of six oil samples selected in function of their chromatographic profiles is reported in detail. The 45 oil compositions were submitted to hierarchical cluster and principal components analysis, which allowed the distinction of three groups within the oil samples. The compositions of the oils from group I (15 samples) and II (12 samples) were dominated by (E)‐β‐caryophyllene and α‐humulene, respectively. Oil samples of group III (18 samples) needed to be partitioned into four subgroups III.1–III.4 whose compositions were dominated by alloaromadenrene, isoguaiene, germacrene B, and δ‐cadinene, respectively.     

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

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

Chemical Composition and Aroma Evaluation of Essential Oils from Evolvulus alsinoides L.

The aim of this study was to investigate the chemical composition and the odor‐active compounds of the essential oils from Evolvulus alsinoides, which is a well‐known edible and medicinal plant. The volatile compounds in the oils were identified by hydrodistillation (HD) and solvent‐assisted flavor evaporation (SAFE) in combination with GC, GC/MS, GC/O (=olfactometry), aroma extract dilution analysis (AEDA), and relative flavor activities (RFA values). The most abundant compound in the HD oil was cis‐α‐necrodol (12.62%), an irregular monoterpene with a cyclopentane skeleton, which is very unusual in the plant kingdom. In the SAFE oil, the main components included 2‐butoxyethanol (9.01%), benzyl alcohol (8.01%), and γ‐butyrolactone (7.37%). Through sensory analysis, 21 aroma‐active compounds were identified by GC/O. The most intense aroma‐active compounds in the HD oil were hexan‐1‐ol and γ‐nonalactone, both of which showed high RFA values. α‐Methyl‐γ‐butyrolactone and dimethyl sulfone contributed more strongly to the aroma of the SAFE oil. These results imply that the essential oils of E. alsinoides deserve further investigation in the food industry.