Chemical Composition and Phytotoxic and Antibiofilm Activity of the Essential Oils of two Moroccan Retama species.

This study reports chemical composition, phytotoxic and antibiofilm activities of essential oils (EOs) of R. dasycarpa and R. sphaerocarpa from Morocco. EOs were analyzed by GC/MS and their phytotoxicities were evaluated against germination and seedling growth of Lolium multiflorum, Sinapis alba and Raphanus sativus. The antimicrobial and anti-biofilm activities were studied against Gram-negative (Pseudomonas aeruginosa, Escherichia coli and Acinetobacter baumannii) and Gram-positive bacteria (Staphylococcus aureus and Listeria monocytogenes). Both EOs were abundant in oxygenated monoterpenes (40.01% and 23.57%, respectively). Carvacrol is the predominant component in R. dasycarpa EO (17.80%), and it also represents an appreciable amount in R. sphaerocarpa (8.96%). R. sphaerocarpa showed total inhibition at high doses against all seeds. S. alba seeds were the most sensitive to all EOs. Minimum inhibitory concentration (MIC) values indicated significant inhibition for R. sphaerocarpa, between 24 and 30 µg/mL, with a remarkable antibacterial potential and biofilm formation inhibition. R. sphaerocarpa EO showed significant biofilm inhibition with variable efficacy depending on the strain and concentration, except for S. aureus. R. dasycarpa exhibited activity against all bacterial strains and effect on metabolism with activity also on mature biofilms. Results suggest that Retama EOs could have potential applications in the fields of food and health.

Characterization of the Phytochemical Composition and Bioactivities of Anacyclus maroccanus Ball. and Anacyclus radiatus Loisel Aerial Parts: Preliminary Evidence for the Possible Development of Moroccan Plants.

In the present study, the phytochemical composition and bioactivities of A. maroccanus (AM) and A. radiatus (AR), two ecotypes collected in the Demnate road and Essaouira regions, respectively, were studied to highlight a pharmacological interest and to enable possible pharmaceutical development. To this end, methanolic and ethyl acetate extracts were prepared for each ecotype by fractionation; next, their phytochemical composition was evaluated by spectrophotometric and chromatographic analysis. Moreover, in line with the available evidence for Anacyclus spp. and their traditional use, a screening of bioactivities, including antioxidant, hypoglycemic, antiglycative, chelating, and antibacterial activities, was performed. The extracts were characterized by high amounts of polyphenols, tannins, and flavonoids, especially in the methanolic extracts; these samples were also enriched in carotenoids despite a lower chlorophyll content. Chlorogenic acid and rutin were the major identified compounds. The extracts also showed interesting hypoglycemic, antiglycative, and antibacterial properties, although with differences in efficacy and potency. Present results provide more scientific basis to the ethnopharmacological uses of Anacyclus spp. and suggest a further interest in AM and AR ecotypes as natural sources of bioactive compounds and/or phytocomplexes for possible pharmaceutical and nutraceutical developments.

Cytotoxic withanolides from the leaves of Moroccan Withania frutescens.

CONTEXT: Withania species are a rich source of interesting phytochemical substances (withanolides) which have shown several biological properties. OBJECTIVE: To investigate the cytotoxic potential of Withania frutescens (L.) Pauquy (Solanaceae) leaf extracts and isolated active compounds against cultured tumor cell lines. MATERIALS AND METHODS: The crude methanol extract of W. frutescens leaves was partitioned with dichloromethane, ethyl acetate and n-butanol. MeOH extract and its fractions were tested for their cytotoxic activity against cancer cell lines (HepG2 and HT29) using the MTT [3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide] assay. Bioassay-guided fractionation was performed for the active CH2Cl2 fraction employing column chromatography and preparative high-performance liquid chromatography. Structural elucidation of the isolated active compounds was carried out mainly by 1D and 2D NMR and mass spectrometry. The compounds were then tested for their cytotoxic activity. RESULTS: The CH2Cl2 fraction was the most active against HT29 cell line. The fractionation procedure resulted in the isolation of 4ß,17α,27-trihydroxy-1-oxo-22-R-witha-2,5,24-trienolide (1), 5ß,6ß-epoxy-4ß,17α,27-trihydroxy-1-oxowitha-2,24-dienolide (2) and 2,3-dihydroxywithaferin A-3ß-O-sulfate (3). The latter exhibited the strongest cytotoxic activity against HT29 cancer cell lines (IC50 of 1.78 ± 0.09 µM) which was comparable to that of 5-fluorouracil (5-FU) used as the positive antimitotic control. DISCUSSION AND CONCLUSION: Compounds 2 and 3 were isolated from W. frutescens for the first time. Data obtained suggest that the sulfated steroidal lactone (3) can be considered as a compound with potential application in the new anticancer drugs development field.

Chemical composition and antioxidant and anticandidal activities of essential oils from different wild Moroccan Thymus species.

Samples of the aerial parts of Thymus broussonetii, T. ciliatus, T. leptobotrys, T. maroccanus, T. pallidus, T. satureioides, and T. serpyllum collected from different natural regions in southern and south-western Morocco were analyzed for their qualitative and quantitative essential oil profiles. In total, 46 compounds, representing more than 99% of the oils, were characterized. Monoterpenes, both hydrocarbons (12.9-58.0%) and oxygenated monoterpenes (38.8-81.1%), were the principal classes of compounds for most of the thyme species studied. Cluster analysis allowed the classification of the species into three main groups: a carvacrol group (Group I), comprising the species T. maroccanus and T. leptobotrys, a linalyl acetate and (E)-nerolidol group (Group II), represented by T. serpyllum, and a thymol and/or carvacrol, γ-terpinene, and p-cymene group (Group III), composed of T. satureioides, T. broussonetii, T. ciliatus, and T. pallidus. The essential oils were screened for their antioxidant and anticandidal activities. The data showed that the oils obtained from T. leptobotrys and T. maroccanus (carvacrol group) possessed the highest antioxidant activities as assessed by the determination of the DPPH free radical-scavenging ability and the ferric-reducing potential. The anticandidal assays indicated that the highest activity was noticed for the essential oil isolated from T. leptobotrys.

Essential oil composition and antimicrobial activity of wild and cultivated Moroccan Achillea ageratum L.: a rare and threatened medicinal species.

The essential oils of leaves and flowers of the wild and cultivated Moroccan Achillea ageratum L., a rare and threatened medicinal species, were examined by GC/MS, and their chemical compositions were compared. At least nine components were identified in both wild and cultivated A. ageratum oils, representing more than 95% of the oils. Artemisyl acetate (62.34-78.79%), yomogi alcohol (4.89-12.40%), santolina alcohol (4.86-11.77%), and artemisia alcohol (3.36-7.04%) were the major compounds. Terpene-alcohol proportion was higher in wild A. ageratum than in cultivated A. ageratum. The antibacterial analysis showed that both oils presented high activity against all the studied Gram-positive strains in a range of MIC values from 2.55 to 7.02 mg/ml, but they appeared not effective against the tested Gram-negative ones (MIC values 20.40-41.10 mg/ml). They also exhibited remarkable antifungal activities against Candida species with MIC values ranging from 5.83 to 8.42 mg/ml. From these results, it was concluded that domestication of this threatened medicinal species using clonal propagation did not significantly affect its chemical composition and consequently its antimicrobial properties.

Chemical Composition, Antioxidant, Antimicrobial and Insecticidal Activities of Essential Oil from a Moroccan Endemic Plant: Bubonium imbricatum.

The chemical composition, antioxidant, antimicrobial and insecticidal properties of essential oil obtained by hydro-distillation from Bubonium imbricatum Cav. have been investigated. The essential oil of aerial parts was analyzed by GC-FID and GC-MS. A total of 63 compounds were identified representing more than 82% of the oil. The major components were cis-chrysanthenyl acetate (31.2%) and thymol isobutyrate (3.4%). The antioxidant activity was evaluated by the DPPH and reducing power test. The data showed moderate activity compared with the reference compounds. Our results showed strong activity of the investigated oil against all tested microorganisms. The highest antibacterial activity was observed against Bacillus subtilis (inhibition zone= 18 ± 0.21, MIC= 0.18 mg/mL). In general, Gram-positive bacteria were more susceptible than Gram-negative ones. Candida parapsilosis was the most sensitive among the Candida strains tested. LD50 and LD90 values were 33.1 and 53.1 ppm against 1-d-old larvae of Aedes aegypti L.

Intraspecific chemical variability of essential oil from leaves of Cupressus atlantica Gaussen, an endemic and endangered coniferous species in Morocco.

The composition of essential oils isolated from leaves of 11 natural populations of Cupressus atlantica, an endemic and endangered coniferous species from Morocco, was investigated by GC-MS. In total, 42 essential oil components were identified, accounting for 73.1-97.7% of the total oil. Monoterpene (25.2-84.9%) and sesquiterpene hydrocarbons (12.2-46.8%) were the principal subclasses of compounds, with α-pinene (15-65.4%), germacrene D (5.9-30.5%), δ-3-carene (2-16.6%) and γ-cadinene (1.3-9.8%) as the main constituents. The results of the oil composition were analysed by hierarchical cluster and principal component analysis that established three main groups of essential oils. These oils were differentiated by the content of the major constituents (α-pinene, germacrene D, δ-3-carene and γ-cadinene), geographical location and climatic characteristics.

Chemical composition and anticandidal properties of the essential oil isolated from aerial parts of Cotula cinerea: a rare and threatened medicinal plant in Morocco.

The chemical composition and anticandidal properties of the essential oil of Moroccan Cotula cinerea aerial parts have been examined. GC-MS data were used to identify 24 constituents. Oxygenated monoterpenes constituted the main fraction with trans-thujone (41.4%), cis-verbenyl acetate (24.7%), 1,8-cineole (8.2%) and camphor (5.5%) as the major components. The anticandidal activity of the essential oil was evaluated using a panel of human pathogenic fungi (Candida albicans CCMM L4 and CCMM L5, C. krusei CCMM L10, C. glabrata CCMM L7 and C. parapsilosis CCMM L18). The oil showed high anticandidal activity against all investigated strains with minimal inhibitory concentrations of 3.2 to 4.7 mg/mL depending on the tested yeast and 5.9 mg/mL as a minimal candidicidal concentration value. These findings add significant information to the pharmacological activity of Cotula cinerea essential oil, which may present a good alternative to antibiotics for the treatment of resistant strains of Candida.