Composition and biological activities of essential oils from four Heracleum species

The composition of essential oils from aerial parts of Heracleum persicum, a widely used medicinal plant, and three other Heracleum species growing wild in Iran were analysed by GC and GC–MS. Myristicin (53.6%), (E)-anethole (25.0%), hexyl butanoate (29.7%) and elemicin (41.1%) were the major compounds of Heracleum pastinacifolium, H. persicum, Heracleum rechingeri and Heracleum transcaucasicum, respectively. Cytotoxic activity assessed on three human cancer cell lines (HeLa, LS180 and Raji), showed that essential oils from H. transcaucasicum (IC₅₀ values; 0.362–0.594 mg/ml) followed by H. pastinacifolium (0.497–1.398 mg/ml) had moderate antitumoral activities. In the DPPH radical scavenging assay, H. pastinacifolium and H. persicum oils showed the highest activities with IC₅₀ values of 7.3 and 7.4 mg/ml, respectively. Antioxidant activity correlated well with the total phenolic content of the oils. None of the essential oils showed significant antimicrobial activities.     

Composition and antimicrobial activity of the essential oils of three Satureja species growing in Tanzania

Hydro-distilled volatile oils from the aerial parts of three Satureja species were investigated, mainly by a combination of GC and GC/MS. One hundred and thirteen compounds were identified, representing 82.9–92.0% of the total oil. Among the identified components, spathulenol, cis-piperitone oxide, α-bisabolol oxide-B, terpinen-4-ol, linalool, bornyl acetate, β-bourbonene, isomenthone, thymol, neoisomenthol and menthone were found as the main components. Furthermore, the essential oils were investigated for their antimicrobial activity, by the agar dilution technique. The antimicrobial test results showed that the oils had a high antimicrobial activity against two Gram-positive and four Gram-negative bacteria, two oral pathogens and three pathogenic fungi. Gram-positive bacteria were more sensitive to the investigated oils than were Gram-negative bacteria. These results could support the suggestion of Satureja species as a source of antimicrobial ingredients for the food industry.     

Phytochemical composition,anti-inflammatory and antitumour activities of four Teucrium essential oils from Greece

The essential oils of four Teucrium species were studied and 150 components, in all, were identified. All oils were rich in sesquiterpenes (50.1–55.8%). Spathulenol and δ-cadinene were the main compounds of Teucrium brevifolium oil; caryophyllene and 4-vinyl guaiacol predominated in Teucrium flavum. Carvacrol and caryophyllene oxide predominated in Teucrium montbretii ssp. heliotropiifolium, while carvacrol and caryophyllene were the most abundant components in Teucrium polium ssp. capitatum. The oil which most effectively inhibited LPS-induced NO production in macrophage cell line RAW 264.7 was that from T. brevifolium (IC₅₀ = 7.1 μg/ml), followed by T. montbretii ssp. heliotropiifolium and T. polium ssp. capitatum (IC₅₀ = 16.5 and 29.4 μg/ml, respectively). The in vitro cytotoxic assay on three human cancer cell lines showed that the most antiproliferative oils were those from T. polium ssp. capitatum and T. montbretii ssp. heliotropiifolium on CACO-2 cell lines (IC₅₀ = 52.7 and 92.2 μg/ml, respectively). The T. brevifolium oil showed a selective cytotoxicity on COR-L23 while significant activity was exerted by T. polium oil on C32.     

Variation in the susceptibility of two Callosobruchus species to essential oils

GC/MS analysis of essential oils extracted from two Cymbopogon species revealed that limonene (23%) and p-mentha-2,8-dien-1-ol in cis (14.3%) and trans (5.6%) forms were the main compounds in Cymbopogon giganteus oil whereas citronellal (31%) and geraniol (24%) were identified in Cymbopogon nardus oil. The toxicity tests performed by fumigation on eggs and adults of Callosobruchus maculatus and Callosobruchus subinnotatus using both essential oils showed a variation in bruchid susceptibility. Essential oil of C. giganteus was more toxic to adults of both bruchid species while essential oil of C. nardus showed the better ovicidal activity. Comparative susceptibility analysis suggested that eggs and adults of C. subinnotatus were two-fold more tolerant to essential oils than C. maculatus in both stages. Oviposition of treated females was strongly reduced in the presence of essential oils. Callosobruchus subinnotatus was more affected than C. maculatus by the essential oil of C. giganteus (oviposition reduction by at least 91% v.s 81% in C. maculatus at 5 μL/L) but the two species were affected similarly by the essential oil of C. nardus.     

Chemical composition and antifungal activity of essential oils from three Himalayan Erigeron species

Three Himalayan Erigeron (Asteraceae) species viz Erigeron mucronatus, Erigeron annuus and Erigeron karwinskianus growing in sub-alpine region revealed occurrence of isomeric polyacetylenic constituents viz., matricaria and lachnophyllum esters which accounted for 83.3%, 69.3% and 30.1% of the essential oils from these species, respectively, in addition to mono- and sesquiterpenoids as minor constituents. The antifungal activity tested by poisoned food (PF) techniques against Fusarium oxysporum, Helminthosporium maydis, Rhizoctonia solani, Alternaria solani and Sclerotinia sclerotiorum demonstrated significant inhibition of the mycelial growth of all strains (p < 0.05). The oils (500 μg/mL) showed significant antifungal effect against tested fungi in the growth inhibition range of 37.6–85.5% with respective IC₅₀ values ranging from 88.8 to 660.0 μg/mL as compared to standard fungicides (100% inhibition) with IC₅₀ value in the range of 32.2–129.4 μg/mL. Significant inhibition of spore germination was noticed for F. oxysporum, Curvularia lunata and Albugo candida which were highly susceptible to E. annuus oil with their IC₅₀ values 120.7, 253.5 and 300.4 μg/mL, respectively. Thus, the results obtained in this study demonstrate the potential of essential oils from Himalayan Erigeron species as non-toxic, eco-friendly and biodegradable natural fungicides.     

Composition and antimicrobial activity of essential oils of Cinnamosma fragrans

Essential oil samples of Cinnamosma fragrans from two regions in Madagascar, Tsaramandroso (38 samples) and Mariarano (30 samples), were analysed by GC/MS. Fifty-seven components were identified, accounting from 88.3% to 99.4% of the oils’ composition. The major components were linalool (72.5 ± 23.3%) in Tsaramandroso and 1,8-cineole (47.3 ± 10.2%) in Mariarano.     

Chemical composition and antimicrobial activity of the essential oils from four Ruta species growing in Algeria

Antimicrobial properties of plants essential oils have been investigated in order to suggest them as potential tools to overcome the microbial drug resistance and the increasing incidence of food borne diseases problems. The aim of this research is to study the antibacterial and antifungal effects of four traditional plants essential oils, Ruta angustifolia, Ruta chalepensis, Ruta graveolens and Ruta tuberculata, against standard bacterial and fungal strains. The chemical compounds of the oils were examined by GC/MS. Results revealed a powerful antifungal activity against filamentous fungi. Aspergillus fumigatus and Cladosporium herbarum are the most sensitive strains to these oils with MIC values less than 3.5 μg ml⁻¹ for certain oils, reaching 7.8 μg ml⁻¹ for other. GC/MS essay exhibited ketones as the most abundant constituent of these oils except for R. tuberculata essential oil which has a completely different composition, monoterpenes alcohols being the most abundant. These compositions explain their potential antifungal activity.     

Chemical composition and antimicrobial properties of essential oils of three Australian Eucalyptus species

The chemical composition and antimicrobial properties of the essential oils of three common Australian Eucalyptus species, namely E. olida, E. staigeriana and E. dives were determined by gas chromatography/mass spectrometry and the agar disc diffusion method, respectively. A total of 24 compounds were identified from the essential oil of E. dives, with the dominant compounds being piperitone (40.5%), α-phellandrene (17.4%), p-cymene (8.5%) and terpin-4-ol (4.7%). For E. staigeriana, 29 compounds were identified with 1,8-cineole (34.8%), neral (10.8%), geranial (10.8%), α-phellandrene (8.8%) and methyl geranate (5.2%) being the dominant ones. In contrast, a single compound, (E)-methyl cinnamate, accounted for 99.4% of the essential oils of E. oilda, although 20 compounds were identified. The essential oils displayed a variable degree of antimicrobial activity with E. staigeriana oil showing the highest activity. In general, Gram-positive bacteria were found to be more sensitive to the essential oils than Gram-negative bacteria. Staphylococcus aureus was the most sensitive strain while Pseudomonas aeruginosa was the most resistant.     

Essential oils of the aerial parts of three Salvia species from Jordan: Salvia lanigera, S. spinosa and S. syriaca

The compositions of the essential oils of three Jordanian Salvia species, S. lanigera and S. spinosa from a desert climate, and S. syriaca from a Mediterranean habitat, were studied. All three oils are rich in monoterpene derivatives (68–73%).     

Chemical and biological characteristics of Cuminum cyminum and Rosmarinus officinalis essential oils

Essential oils extracted by hydrodistillation from Cuminum cyminum and Rosmarinus officinalis were characterized by means of GC and GC–MS. C. cyminum and R. officinalis contained α-pinene (29.1%, 14.9%), 1,8-cineole (17.9%, 7.43%) and linalool (10.4%, 14.9%), respectively, as the major compounds. C. cyminum oil exhibited stronger antimicrobial activity than did R. officinalis oil against E. coli, S. aureus and L. monocytogenes. Complete death time on exposure to Cuminum cyminum L. and Rosmarinus officinalis L. oils were 20 and 25 min 180 and 240 min and 90 and 120 min for E. coli, S. aureus and L. monocytogenes, respectively. Radical-scavenging and antioxidant properties were tested by means of 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay and the β-carotene bleaching test. These properties were compared to those of Thymus x-porlock essential oil, used as a reference ingredient. The radical scavenging performance of the rosemary oil was better than that of C. cyminum. Results from the antioxidant test were better than those provided by the radical-scavenging activity. C. cyminum and R. officinalis essential oils may be considered as potent agents in food preservation.     

Comparative chemical composition,free radical-scavenging and cytotoxic properties of essential oils of six Stachys species from different regions of the Mediterranean Area

The chemical composition of essential oils of six Stachys species, S. cretica L. ssp. vacillans Rech. fil., S. germanica L., S. hydrophila Boiss., S. nivea Labill., S. palustris L. and S. spinosa L., obtained by hydrodistillation, was studied by GC and GC–MS. All the oils have in common a great percentage of fatty acids and esters (24.2–58.5%) and a high amount of sesquiterpenes (16–35.9%), with the exception of the oil from S. palustris, which consisted mainly of carbonylic compounds (25.4%). The antioxidant activity by DPPH test and the antiproliferative activity on a series of human cancer cell lines (C32, amelanotic melanoma and ACHN, renal cell adenocarcinoma) were investigated for all the oils. S. palustris,S. cretica and S. hydrophila showed the highest antiradical effect, with IC₅₀ values of 0.482, 0.652 and 0.664 mg/ml, respectively. The most antiproliferative essential oil against C32 cell line was the oil of S. germanica with a 77% of inhibition at a concentration of 100 μg/ml. S. germanica, S. palustris and S. spinosa showed the most antiproliferative activity on ACHN cell line, at a concentration of 100 μg/ml,with 81%, 77% and 73% inhibition, respectively.     

Chemical composition,antioxidant and antibacterial activities of the essential oils isolated from Tunisian Thymus capitatus Hoff. et Link.

The chemical composition, antioxidant and antibacterial activities of essential oils isolated by hydrodistillation from the aerial parts of Tunisian Thymus capitatus Hoff. et Link. during the different phases of the plant development, and from different locations, were evaluated. The chemical composition was analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The main components of the essential oils were carvacrol (62–83%), p-cymene (5–17%), γ-terpinene (2–14%) and β-caryophyllene (1–4%). The antioxidant activity of the oils (100–1000 mg l⁻¹) was assessed by measurement of metal chelating activity, the reductive potential, the free radical scavenging (DPPH) and by the TBARS assay. The antioxidant activity was compared with that of synthetic antioxidants: butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). Both the essential oils and BHA and BHT showed no metal chelating activity. Although with the other methodologies, there was a general increase in the antioxidant activity, with increasing oil concentration, maxima being obtained in the range of 500 and 1000 mg l⁻¹ for flowering and post-flowering phase oils. Major differences were obtained according to the methodology of antioxidant capacity evaluation. Antibacterial ability of Th. capitatus essential oils was tested by disc agar diffusion against Bacillus cereus, Salmonella sp., Listeria innocua, four different strains of Staphylococus aureus (C15, ATCC25923, CFSA-2) and a multi-resistant form of S. aureus (MRSA-2). Antibacterial properties were compared to synthetic antibiotics. Higher antibacterial activity was observed with the flowering and the post-flowering phase essential oils.     

Composition,cytotoxicity and antimicrobial activity of essential oil from Dictamnus dasycarpus

The composition of the essential oil from Dictamnus dasycarpus was analysed by GC–MS; 47 constituents (88.9% of the total oil) were identified. The main compounds were syn-7-hydroxy-7-anisylnorbornene (29.4%), pregeijerene (15.5%) and geijerene (11.4%). The antimicrobial activity of the essential oil was evaluated against nine microorganisms using disc diffusion and broth microdilution methods. The oil showed the strongest bactericidal activity against Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus. The in vitro cytotoxicity of the oil on six human cancer cell lines was also examined. The cytotoxicity of the oil on three human breast cancer cell lines was significantly stronger than on other cell lines.     

Screening of the antioxidative and antimicrobial properties of the essential oils of Pimpinella anisetum and Pimpinella flabellifolia from Turkey

The aerial parts of two endemic Pimpinella [Pimpinella anisetum Boiss. & Ball. and Pimpinella flabellifolia (Boiss.) Benth. ex Drude] were hydro-distilled to produce oils in the yields of 2.07% (v/w) and 2.61% (v/w), respectively. The oils were analysed by GC and GC/MS. Twenty-one and nineteen components were identified, representing 99.5% and 99.7% of the oils, respectively. The main compounds of P. anisetum were (E)-anethole (82.8%) and methyl chavicol (14.5%), whereas limonene (47.0%), (E)-anethole (37.9%) and α-pinene (6.0%) were the major constituents of P. flabellifolia. The oils were screened for their possible antioxidant activities by two complementary test systems, namely DPPH free radical-scavenging and β-carotene/linoleic acid systems. In the first case, P. anisetum oil exerted greater antioxidant activity than that of P. flabellifolia oil with an IC₅₀ value of 5.62 ± 1.34 μg/ml. In the β-carotene/linoleic acid test system, the oil of P. anisetum was superior to P. flabellifolia with 70.5% ± 2.86 inhibition rate. Essential oils of the plants studied here were also screened for their antimicrobial activities against six bacteria and two fungi. The oils showed moderate antimicrobial activity against all microorganisms tested.     

Citrus paradisi and Citrus sinensis flavonoids: Their influence in the defence mechanism against Penicillium digitatum

Citrus peel is rich in flavanone glycosides and polymethoxyflavones. In view of their importance for industrial application as well as for their pharmacological properties, their content was analyzed in the mature fruits of several Citrus paradisi (grapefruit) and Citrus sinensis (orange) varieties, with a view to select the most interesting for isolation. The results shows that the Star Ruby grapefruit and the Sanguinelli orange stand out for their high contents of naringin and hesperidin, respectively. The presence of the polymethoxyflavones nobiletin, heptamethoxyflavone and tangeretin, could be ascertained in all the grapefruit varieties analysed. Higher polymethoxyflavone levels were recorded in orange, with Valencia Late showing the greatest nobiletin, sinensetin and tangeretin contents and Navelate the highest heptamethoxyflavone levels. An in vitro study revealed that these compounds acted as antifungal agents against Penicillium digitatum, the polymethoxyflavones being more active than the flavanones in this respect. The possible participation of these phenolic compounds in the defence mechanism of Citrus against P. digitatum is discussed.     

Antibacterial activity and chemical composition of 20 Eucalyptus species’ essential oils

The essential oils of twenty Eucalyptus species harvested from Zerniza and Souinet arboreta (North West and North of Tunisia), were screened for their antibacterial activities by the agar disc diffusion method. Eighteen major compounds, identified by GC and GC/MS, have been retained for the study of the chemical and biological activity variability. The main ones were 1,8-cineole followed by α-pinene, p-cymene, borneol, cryptone, spathulenol, viridiflorol and limonene. The chemical principal components analysis identified 10 chemotypes, however that of the inhibition zone diameter (izd) of growth bacteria separated 5 groups of Eucalyptus oils, characterised by their antibacterial inhibition ability. The most sensitive strain was the Gram positive Staphylococcus aureus with that of E. odorata oil (16.0 ± 1.0 mm izd), while the most resistant bacteria was Pseudomonas aeruginosa. Some correlation between the amount of 1,8-cineole, p-cymene, α-pinene, or of cryptone and the antibacterial activity were observed.     

Terpenoids and hexenes from the leaves of Crataegus pinnatifida

Crataegus pinnatifida have long been used in traditional Chinese medicine and European herbal medicine, and are widely consumed as food, in the form of juice, drink, jam and canned fruit. Four new compounds, a sesquiterpene and its glycoside (1–2), two monoterpene glycosides (3–4), together with eight known compounds (5–12), were isolated from the leaves of C. pinnatifida. Their structures were elucidated as (5Z)-6-[5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl]-3-methylhexa-1,5-dien-3-ol (1), (5Z)-6-[5-(2-O-β-d-glucopyranosyl-propan-2-yl)-2-methyl tetrahydrofuran-2-yl]-3-methylhexa-1,5-dien-3-ol (2), 5-ethenyl-2-[2-O-β-d-glucopyranosyl-(1″ → 6′)-β-d-glucopyranosyl-propan-2-yl]-5-methyltetrahydrofuran-2-ol (3), 4-[4β-O-β-d-xylopyranosyl-(1″ → 6′)-β-d-glucopyranosyl-2,6,6-trimethyl-1-cyclohexen-1-yl]-butan-2-one (4), (Z)-3-hexenyl O-β-d-glucopyranosyl-(1″ → 6′)-β-d-glucopyranoside (5), (Z)-3-hexenyl O-β-d-xylopyranosyl-(1″ → 6′)-β-d-glucopyranoside (6), (Z)-3-hexenyl O-β-d-rhamnopyranosyl-(1″ → 6′)-β-d-glucopyranoside (7), (3R,5S,6S,7E,9S)-megastiman-7-ene-3,5,6,9-tetrol (8), (3R,5S,6S,7E,9S)-megastigman-7-ene-3,5,6,9-tetrol9-O-β-d-glucopyranoside (9), (6S,7E,9R)-6,9-dihydroxy-4,7-megastigmadien-3-one 9-O-[β-d-xylopyranosyl-(1″ → 6′)-β-d-glucopyranoside] (10), Linarionoside C (11), and (3S,9R)-3,9-dihydroxy-megastigman-5-ene 3-O-primeveroside (12), using a combination of mass spectroscopy, 1D and 2D NMR spectroscopy and chemical analysis. Cytotoxicity of the new compounds was assayed against selected human glioma (U87) cell lines.     

Phytochemical composition and antimicrobial activities of the essential oils from Satureja subspicata Vis. growing in Croatia

The present study describes the phytochemical profile and antimicrobial activity of Satureja subspicata Vis. essential oils, collected in Dalmatia (Croatia). Three samples of essential oils were obtained from the aerial parts of the plant by hydrodistillation and analyzed by GC–MS. From the 24 compounds representing 97.47% of the oils, carvacrol (16.76%), α-pinene (13.58), p-cymene (10.76%), γ-terpinene (9.54%) and thymol methyl ether (8.83%) appear as the main components. The oils also contained smaller percentages of myrcene, linalool, β-caryophyllene, limonene, geranyl acetate, 1-Octen-3-ol, nerol, thymol and borneol. Furthermore, antimicrobial activity of the oil was evaluated using agar diffusion and broth microdilution methods. The antimicrobial test results showed that the oils had a great potential antimicrobial activity against all 13 bacteria and 9 fungal strains. Gram-positive bacteria are more sensitive to the investigated oil, with a range of 0.09 to 6.25 μl/ml than Gram-negative bacteria in the range which is significantly higher from 1.56 to 25.00 μl/ml. Results presented here may suggest that the essential oil of S. subspicata possesses antimicrobial properties, and is therefore a potential source of antimicrobial ingredients for the food and pharmaceutical industry.     

Composition of the essential oil of Daucus gingidium L. ssp. gingidium

The essential oils obtained from leaves and fruits of Daucus gingidium ssp. gingidium have been studied. The main constituents of the essential oil from the leaves were sabinene (26.8%), α-pinene (10.8%), germacrene D (6.9%) and limonene (5.7%). Sabinene (60.6%) was the main compound identified in the essential oil of the fruits, followed by α-pinene (12.2%) and 4-terpineol (5.4%). Furthermore, qualitative and quantitative considerations about differences with literature data on Daucus carota have been made in order to confirm the species status of D. gingidium.     

Antibacterial activity of the essential oils of Salvia officinalis L. and Salvia triloba L. cultivated in South Brazil

The essential oils of Salvia officinalis and Salvia triloba cultivated in South Brazil were analyzed by GC–MS. The major constituents of the oil of S. officinalis were α-thujone, 1,8-cineole, camphor, borneol and β-pinene, whereas those of S. triloba were α-thujone, 1,8-cineole, camphor, and β-caryophyllene. The essential oils of both species exhibited remarkable bacteriostatic and bactericidal activities against Bacillus cereus, Bacillus megatherium, Bacillus subtilis, Aeromonas hydrophila, Aeromonas sobria, and Klebsiella oxytoca. Moreover, the essential oil of S. triloba efficiently inhibited the growth of Staphylococcus aureus. S. aureus and A. hydrophila growth were drastically reduced even in the presence of 0.05 mg/ml of the essential oil of S. triloba.