Flavonoids from Plinia cauliflora (Mart.) Kausel (Myrtaceae) with antifungal activity

Plinia cauliflora is a plant species with edible fruits but its chemical composition is not totally known yet although former studies showed its potential as antifungal agent. This work aimed the chemical analysis of the leaves, the activity against fungi species and evaluated cytotoxicity. Extract was obtained with 70% ethanol. An ethyl acetate fraction was obtained and glycosylated quercetin and myricetin were isolated. Samples were tested against Candida species, dermatophytes and entomopathogenic fungi. Cytotoxicity was evaluated against fibroblast cells. Extract showed good activity against C. albicans (minimum inhibitory concentration at 156 μg/mL), C. parapsilosis (78 μg/mL), C. krusei (19 μg/mL), Trichophyton rubrum (78 μg/mL) and Microsporum canis (156 μg/mL). Isolated compounds were more active against C. krusei and T. rubrum. The extract, which was the more active sample, demonstrated low cytotoxic effect and encourage more studies against rising non-albicans species and dermatophyte T. rubrum.     

Chemical composition and in vitro antibacterial and antiproliferative activities of the essential oil from the leaves of Psidium myrtoides O. Berg (Myrtaceae)

In this study, the chemical composition and antibacterial and antiproliferative potential of the essential oil obtained from fresh leaves of Psidium myrtoides (PM-EO) against oral pathogens and human tumour cell lines were investigated for the first time. GC-FID and GC-MS analyses showed that trans-β-caryophyllene (30.9%), α-humulene (15.9%), α-copaene (7.8%), caryophyllene oxide (7.3%) and α-bisabolol (5.3%) are the major constituents of PM-EO. The antibacterial activity of PM-EO against a panel of oral pathogens was investigated in terms of their minimal inhibitory concentrations (MIC) using the broth microdilution method. PM-EO displayed moderate activity against Streptococcus mitis (MIC = 100 μg/mL), S. sanguinis (MIC = 100 μg/mL), S. sobrinus (MIC = 250 μg/mL), and S. salivarius (MIC = 250 μg/mL), and strong activity against S. mutans (MIC = 62.5 μg/mL). The antiproliferative activity in normal (GM07492A, lung fibroblasts) and tumour cell lines (MCF-7, HeLa, and M059 J) was performed using the XTT assay. PM-EO showed 50% inhibition of normal cell growth at 359.8 ± 6.3 μg/mL. Antiproliferative activity was observed against human tumour cell lines, with IC₅₀ values significantly lower than that obtained for the normal cell line, demonstrating IC₅₀ values for MCF-7 cells (254.5 ± 1.6 μg/mL), HeLa cells (324.2 ± 41.4 μg/mL) and M059 J cells (289.3 ± 10.9 μg/mL). Therefore, the cytotoxicity of PM-EO had little influence on the antibacterial effect, since it showed antibacterial activity at lower concentrations. Our results suggest that PM-EO is a promising source of new antibacterial and antitumour agents.     

Antidiarrhoeic effect of Eugenia dysenterica DC (Myrtaceae) leaf essential oil

Essential oil from Eugenia dysenterica leaves was able to inhibit both the diarrhoea and enteropooling induced by castor oil; however, the distance travelled by charcoal meal in the intestine was not change. These data suggest that the antidiarrhoeic effect of the essential oil from E. dysenterica leaves is related to its ability to inhibit intestinal secretion and/or to increase intestinal absorption.     

Antimycoplasmic activity and seasonal variation of essential oil of Eugenia hiemalis Cambess. (Myrtaceae)

The purpose of this work was to study the chemical composition and antimycoplasmic and anticholinesterase activities of the essential oil of Eugenia hiemalis leaves collected throughout the year. A total of 42 compounds were identified by CG, and are present in almost every seasons. Sesquiterpenes were dominant (86.01–91.48%), and non-functionalised sesquiterpenes comprised the major fraction, which increased in the summer; monoterpenes were not identified. The major components were spathulenol (5.36–16.06%), δ-cadinene (7.50–15.93%), bicyclogermacrene (5.70–14.24%) and β-caryophyllene (4.80–9.43%). The highest oil yield was obtained in summer and autumn. Essential oils presented activity against three evaluated Mycoplasma strains, but no activity was observed in the anticholinesterase assay.     

Myrcia paivae O.Berg (Myrtaceae) Essential Oil,First Study of the Chemical Composition and Antioxidant Potential

The Myrtaceae family is one of the most representative in the Amazon. Several species have high added-value pharmacological potential. In order to contribute to the knowledge of the aromatic profile of Myrtaceae species from the Amazon, the present study presents the first report on the productivity, chemical composition, and antioxidant profile of the essential oil (EO) of Myrcia paivae. Dry leaves of the species were submitted to hydrodistillation to obtain their EO. The EO performance was calculated on a moisture-free basis and the analysis of the chemical profile was carried out by GC/MS. The determination of the antioxidant capacity was assessed by means of the antioxidant capacity equivalent to the inhibition Trolox of the ABTS^•+ and DPPH^• radicals. The results indicate that EO performance was equivalent to 1.69%. As for the chemical composition, hydrocarbon monoterpenes were predominant in the sample (>77%); terpinolene (14.70%), α-phellandrene (14.69%), γ-terpinene (9.64%), sylvestrene (7.62%), α-thujene (6.46%), and α-pinene (6.39%) were the constituents with higher content. Regarding the antioxidant capacity, the results show that the EO presented good results in the inhibition of ABTS^•+ (0.886 ± 0.226 mM L⁻¹) and DPPH^• (2.90 ± 0.083 mM L⁻¹), which can be attributed to the high monoterpene content in the sample.     

Chemical composition and biological assays of essential oils of Calamintha nepeta (L.) Savi subsp. nepeta (Lamiaceae)

Aerial parts of wild Calamintha nepeta (L.) Savi subsp. nepeta growing spontaneously on the Mediterranean coast (Sardinia Island, Italy) and on the Atlantic coast (Portugal) were used as a matrix for the supercritical extraction of volatile oil with CO(2). The collected extracts were analysed by GC-FID and GC-MS methods and their compositions were compared with that of the essential oil isolated by hydrodistillation, but the differences were not relevant. A strong chemical variability was observed in the essential oils depending on the origin of the samples. The results showed the presence of two chemotypes of C. nepeta. In all Italian samples, pulegone, piperitenone oxide and piperitenone were the main components (64.4-39.9%; 2.5-19.1%; 6.4-7.7%); conversely, the oil extracted from Portuguese C. nepeta is predominantly composed of isomenthone (35.8-51.3%), 1,8-cineole (21.1-21.4%) and trans-isopulegone (7.8-6.0%). The minimal inhibitory concentration (MIC) and the minimal lethal concentration (MLC) were used to evaluate the antifungal activity of the oils against Candida albicans, Candida tropicalis, Candida krusei, Candida guillermondii, Candida parapsilosis, Cryptococcus neoformans, Trichophyton rubrum, Trichophyton mentagrophytes, Microsporum canis, Microsporum gypseum, Epidermophyton floccosum, Aspergillus niger, Aspergillus fumigatus and Aspergillus flavus. The Italian oil, rich in pulegone, exhibited significant antifungal activity against Aspergillus and dermatophyte strains, with MIC values of 0.32-1.25 μL mL(-1).     

Chemical and biological analyses of the essential oils and main constituents of Piper species

The essential oils obtained from leaves of Piper duckei and Piper demeraranum by hydrodistillation were analyzed by gas chromatography-mass spectrometry. The main constituents found in P. demeraranum oil were limonene (19.3%) and β-elemene (33.1%) and in P. duckei oil the major components found were germacrene D (14.7%) and trans-caryophyllene (27.1%). P. demeraranum and P. duckei oils exhibited biological activity, with IC(50) values between 15 to 76 μg mL(-1) against two Leishmania species, P. duckei oil being the most active. The cytotoxicity of the essential oils on mice peritoneal macrophage cells was insignificant, compared with the toxicity of pentamidine. The main mono- and sesquiterpene, limonene (IC(50) = 278 μM) and caryophyllene (IC(50) = 96 μM), were tested against the strains of Leishmania amazonensis, and the IC(50) values of these compounds were lower than those found for the essential oils of the Piper species. The HET-CAM test was used to evaluate the irritation potential of these oils as topical products, showing that these oils can be used as auxiliary medication in cases of cutaneous leishmaniasis, with less side effects and lower costs.     

Chemical composition and biological activities of essential oils of two new chemotypes of Glebionis Cass.

This paper includes the result of the first study of the chemical composition, antioxidant, antiinflammatory, and antidiabetic activities of the essential oils of Glebionis coronaria (L.) Cass. ex Spach and Glebionis segetum (L.) Fourr. from Turkey. In the current study, nine and twenty-eight constituents were determined in the essential oils of aerial parts of G. coronaria (GCE) (92.1%) and G. segetum (GSE) (90.0%), respectively. The main components were capillin (65.9%) in GCE, capillene (53.4%) in GSE. The essential oil compositions were evaluated and compared with previous researches. In the current study, the plants are classified as chemotypes of Glebionis species. GCE and GSE showed poor and very poor DPPH radical scavenging activity, respectively. GCE and GSE exhibited significant and strong antiinflammatory activity against the 5-lipoxygenase enzyme, respectively. Also, GCE and GSE displayed moderate and weak antidiabetic activity against the α-glucosidase enzyme, respectively. Polyacetylenes were determined as the main class of compounds in GCE and GSE and had a notable antiinflammatory activity.     

Composition of essential oils from two endemicSideritis species of Turkey

The genus Sideritis is represented in Turkey by 46 species and altogether 53 taxa of these being endemic in Turkey (74%) [1–3].Published in Khimiya Prirodnykh Soedinenii, No. 1, pp. 76–80, January–February, 1999.     

Chemical composition and phytotoxic effects of essential oils from four Teucrium species

The essential oils of four Teucrium species were studied and 131 components, in all, were identified. All oils were rich in sesquiterpenes (50.0-61.9%). Caryophyllene and caryophyllene oxide were the main components of Teucrium arduini; germacrene D, delta-cadinene and gamma-cadinene predominated in Teucrium maghrebinum. Carvacrol and caryophyllene predominated in Teucrium polium ssp. capitatum, while carvacrol, caryophyllene oxide and caryophyllene were the most abundant components in Teucrium montbretii ssp. heliotropiifolium. The germination of radish and garden cress was less sensitive to the four essential oils. The radicle elongation, above all, of radish was significantly inhibited by all oils, in particular by the essential oil of T. arduini, at the highest doses tested. Among the main components of the oils, monoterpenes resulted the more active compounds.     

Chemistry and biological activity of essential oils from Piper claussenianum (Piperaceae)

Analyses of essential oils obtained from fresh and dried leaves and inflorescences of Piper clausenianum were performed using GC-FID, GC-MS and NMR techniques. Forty compounds were detected for these four oils with the total of identified constituents ranging from 88.7% for the dried inflorescences to 97.7% for the dried leaves. Sesquiterpenes were the main constituents in the volatile fraction from leaves with a high percentage of (E)-nerolidol (up to 83%). However, monoterpenes were identified in greater amount in the inflorescences, with linalool percentages from 50% up. The essential oils from fresh leaves and inflorescences were submitted to anti-parasitic activity against a strain of Leishmania amazonensis. Both samples showed biological activity, but the essential oil from P. claussenianum fresh leaves, which was rich in (E)-nerolidol, showed effective growth inhibition of L. amazonensis due to the high percentage of this metabolite in the mixture.     

Chemical composition and antioxidant activities of essential oils and methanol extracts of three wild Lavandula L. species

A comparative study of essential oil composition, polyphenol content and antioxidant activities of Lavandula coronopifolia, Lavandula multifida and Lavandula stoechas subsp. stoechas were reported. Qualitative and quantitative variations in the composition of oils according to species were shown. Lavandula coronopifolia's oil was characterised by high proportions of trans-β-ocimene (26.9%), carvacrol (18.5%), β-bisabolene (13.1%) and myrcene (7.5%). The main components of L. multifida oil are carvacrol (65.1%) and β-bisabolene (24.7%). Lavandula stoechas oil is rich in fenchone (34.3%) and comphor (27.4%). The total phenolic and flavonoid contents also significantly varied among species. Lavandula coronopifolia exhibits the highest phenolic and flavonoid contents (31.3?mg GAE?g(-1) and 16.3?mg RE?g(-1), respectively), followed by L. multifida (30.8?mg GAE?g(-1) and 12.3?mg RE?g(-1)). Methanolic extracts and essential oils displayed significant antioxidant activities. The level of antioxidant capacity varied according to extracts and species.     

Chemical composition and biological activities of essential oils of Pinus patula

Essential oils isolated from needles of Pinus patula by hydrodistillation were analyzed by gas chromatography-flame ionization detection (GC-FID) and gas chromatography mass spectrometry (GC-MS). Thirty-eight compounds were identified, representing 98.3% of the total oil. The oil was rich in monoterpene hydrocarbons (62.4%), particularly alpha-pinene (35.2%) and beta-phellandrene (19.5%). The in vitro antifungal assay showed that P. patula oil significantly inhibited the growth of 9 plant pathogenic fungi. The oil, when tested on Sinapis arvensis, Lolium rigidum, Phalaris canariensis and Trifolium campestre, completely inhibited seed germination and seedling growth of all species. Our preliminary results showed that P. patula essential oil could be valorized for the control of weeds and fungal plant diseases.     

Chemical composition and evaluation of the antimicrobial activity of the essential oil from leaves of Eugenia platysema

This study describes the qualitative and quantitative chemical composition and evaluates the antibacterial activity of essential oil from Eugenia platysema leaves. Analysis by GC–FID and GC–MS allowed the identification of 22 compounds. Different from the other species of the Eugenia genus, the major compound found in the essential oil was the diterpene phytol (66.05%), being this the first report of the presence of this compound in the essential oils from Eugenia genus. The sesquiterpene elixene was the second most concentrated compound in the studied essential oil (9.16%). The essential oil from E. platysema was tested for its antibacterial activity against cell-walled bacteria and mollicute strains of clinical interest using the microdilution broth assay. The results showed that the essential oil of E. platysema was inactive until 1000 μg mL^?1 against tested bacteria.     

Chemical diversity and anti-acne inducing bacterial potentials of essential oils from selected Elsholtzia species

Essential oils from the aerial parts of four Elsholtzia species; Elsholtzia stachyodes, Elsholtzia communis, Elsholtzia griffithii and Elsholtzia beddomei were obtained by steam distillation and their chemical components were analysed by gas chromatography-mass spectrometry (GC-MS). Principle Component Analysis was used to identify the chemical variations in the essential oils from these plants, which could be categorised into two groups according to their main chemical components which are acylfuran derivatives and oxygenated monoterpenes. Additionally, the anti-acne inducing bacterial activity against Staphylococcus aureus and Staphylococcus epidermidis were evaluated. The oil from E. stachyodes was the most efficacious against the growth of S. aureus and S. epidermidis having MIC values of 0.78 and 1.56 μL/mL, respectively, and exhibited five times more effective than erythromycin (standard antibiotic).     

Chemical composition and biological activities of essential oil from Filifolium sibiricum (L.) Kitam

The essential oil from Filifolium sibiricum (L.) Kitam were extracted using hydrodistillation and GC-MS was used to analyse the essential oil. The main components were espatulenol (8.55%), geranyl acetate (8.03%), caryophyllene oxide (5.47%), calamenene (4.79%), geraniol (4.28%), calamenene (4.53%), geraniol (4.06%), cedrene epoxide (3.23%), myrtenol (3.18%), transgeranylgeranio (3.13%), etc. The essential oil showed intensive inhibitory effects against MCF-7 with IC₅₀ level of 0.78 mg/mL, HepG-2 with IC₅₀ level of 0.44 mg/mL, SKOV-3 with IC₅₀ level of 0.27 mg/mL, BGC-823 with IC₅₀ level of 0.34 mg/mL. In the antibacterial test, the essential oil showed the significant antibacterial activities. The MIC and MBC values were 5.20 and 5.20 mg/mL against Staphylococcus aureus.     

Comparative study of composition and biological activities of SDE prepared essential oils from flowers and fruits of two Hypericum species from central Iran

Essential oil (EO) compositions of flowers and fruits of Hypericum perforatum L. and Hypericum scabrum L. growing wild in Kashan, central Iran, were determined by simultaneous steam distillation-solvent extraction method and analysed using GC-MS technique. Analysis revealed 28 identified compounds for H. perforatum, with two main components being α-pinene (25.36%) and α-amorphene (12.12%). Thirty-five compounds were identified in H. scabrum L. representing 98.60% of the oil with α-pinene (70.21%) and p-mentha-1,5-dien-8-ol (2.89%) as main components. Some new compounds were found in significant quantities which were not found in other chemotypes. The antioxidant activities of the EOs evaluated for the first time in this study using β-carotene bleaching and DPPH assays seemed to be attributed directly to α-pinene contents in them. Antibacterial activities of both mentioned EOs were higher than that of their main constituent, α-pinene, against Staphylococcus aureus and Escherichia coli.     

Chemical composition,phytotoxic and antifungal properties of Ruta chalepensis L. essential oils

The chemical composition, and phytotoxic and antifungal activities of the essential oils isolated by using hydrodistillation from the aerial parts of Tunisian rue were evaluated. Significant variations were observed among harvest periods. The analysis of the chemical composition by gas chromatography/mass spectrometry showed that 2-undecanone (33.4–49.8%), 2-heptanol acetate (13.5–15.4%) and α-pinene (9.8–11.9%) were the main components. The antifungal ability of rue essential oils was tested by using disc agar diffusion against ten plant pathogenic fungi. A high antifungal activity was observed for the essential oil isolated at flowering developmental phase. Furthermore, rue essential oils showed high level of herbicidal activity against several weeds.