[show abstract][hide abstract] ABSTRACT: This study describes the antioxidant and insecticidal activities of essential oils (EOs) of Mentha suaveolens
subsp. timija, Thymus satureioides, Achillea ageratum, Cotula cinerea and Salvia officinalis widely used in
Morocco as flavorings, food additives and preservatives. Sixty seven components were identified accounting for more than 95.0 % of the total oils. M. suaveolens subsp. timija oil had as main components menthone and pulegone. A. ageratum oil was particularly rich in artemisyl acetate and yomogi alcohol. The essential oil of T. satureioides was characterized by high contents of carvacrol and borneol. C. cinerea oil contained trans-thujone and cis-verbenyl acetate as major constituents, whereas S. officinalis oil was characterized
by trans-thujone and camphor. Antioxidant activities were examined by means of 2,2-diphenyl-1-
picrylhydrazyl radical (DPPH), reducing power, β-carotene/linoleic acid bleaching and ABTS radical tests.
In all assays, the highest antioxidant potency was observed in T. satureioides EO with IC50 values ranging
from 0.15±0.36 μg mL-1 to 0.23±0.67 μg mL−1 across the four assays. The in vitro evaluation of the insecticidal activity showed that M. suaveolens subsp. timija EO present the highest insecticidal efficiency against adults of Tribolium castaneum with LD50 and LD90 values of 0.17 μL cm−2 and 0.26 μL cm−2, respectively, and LT50, LT90 values ranged from 44.19 h to 2.98 h and 98.14 h to 6.02 h, respectively. Our data support the possible use of T. satureioides oil as potential antioxidant agent, while M. suaveolens subsp. timija oil can be developed as a new natural bio-insecticide.
Journal of Food Science and Technology -Mysore- 02/2014; · 1.12 Impact Factor
[show abstract][hide abstract] ABSTRACT: The chemical composition, antioxidant and antimicrobial activities of essential oils isolated by hydrodistillation from the aerial parts of wild endemic Moroccan Thymus maroccanus at different developmental stages (vegetative, flowering and post-flowering) were evaluated. The yield of essential oils (v/w%) based on dry weight at different stages were: vegetative (2.14%), flowering (leaves: 1.80%; flowers: 3.46%), and post-flowering (leaves: 0.98%; post-flowers: 2.46%). Analysis of the essential oils by GC/MS revealed the presence of 28 components represented mainly by monoterpenes, both oxygenated (59.4–79.4%) and hydrocarbons (14.3–34.2%). The ranges of major constituents were as follow: carvacrol (14.1–77.6%), p-cymene (3.5–7.9%), γ-terpinene (3.8–6.6%) and α-pinene (1.2–7.8%). Leaves at post-flowering stage also contained a significant amount of borneol (16.3%) and thymol (27.8%). Essential oils obtained from flowering stage showed the highest antioxidant activity as measured by DPPH free radical scavenging ability, reductive potential and β-carotene/linoleic acid assays with IC50 values ranging from 61.48 ± 1.58 μg/mL to 182.86 ± 2.84 μg/mL for leaves and from 63.81 ± 1.96 μg/mL to 129.93 ± 6.16 μg/mL for flowers. The essential oils were also screened for antimicrobial activity against seven bacteria of significant importance for food hygiene and four pathogenic fungal strains. The results indicated that Candida strains were the most sensitive among the microorganisms tested (MIC values of 0.12–0.25 mg/mL) followed by Gram positive and Gram negative bacterial strains, with the Gram-negative Pseudomonas aeruginosa being the most resistant strain. The maximum antimicrobial activity was observed with oils obtained from the vegetative and flowering stages, which therefore represent the optimal harvesting times of this plant for application in the pharmaceutical and food industries.
Industrial Crops and Products 01/2013; 49. · 2.47 Impact Factor
[show abstract][hide abstract] ABSTRACT: 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.
[show abstract][hide abstract] ABSTRACT: 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.
Natural product research 03/2012; · 1.01 Impact Factor
[show abstract][hide abstract] ABSTRACT: 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.
[show abstract][hide abstract] ABSTRACT: The title compound, C(20)H(28)O(3), was isolated during our investigation into the chemical composition and pharmacological activity of Centipeda cunninghamii (DC.) A. Braun & Asch. (Asteraceae). The enanti-opure compound, a diterpene with a carbon skeleton, is composed of three six- and one five-membered rings in chair, twist-boat, half-chair and envelope conformations, respectively. Each mol-ecule makes one intra- and one inter-molecular O-H⋯O hydrogen bond in the crystal lattice, forming hydrogen-bonded chains along . The absolute configuration of the compound was assigned on the basis of optical rotation measurements.
[show abstract][hide abstract] ABSTRACT: Wheat bran has been widely recognised as a cancer preventive agent, although the mechanism of the protection is not yet fully understood. Some reports suggested that, for the protection, lipophilic phytochemicals from the bran were more important than the physiological function of bran fibre. Wheat bran lipophilic extracts were scrutinised using bioactivity-guided fractionation (HPLC) against the growth of human prostate adenocarcinoma (PC3) cells. The fractions containing unsaturated free fatty acid, phytosteroids and alkylresorcinols exerted high cytotoxic activity. Detailed research of the alkylresorcinol fraction isolated seven pure compounds, four of them with strong inhibitory properties against the growth of PC3 cells, including 5-heptadecylresorcinol (IC50 = 22.5 μg/ml), 5-(16-heneicosenyl)resorcinol (trans) (IC50 = 13.7 μg/ml), 5-(14-nonadecenyl)resorcinol (trans) (IC50 = 42.2 μg/ml) and 5-(2-oxotricosanyl)resorcinol (IC50 = 10.9 μg/ml). The alkylresorcinols in wheat bran were quantified using a Single Ion Monitoring (SIM) method developed on LC-MS. The active alkylresorcinols were found to be minor components in wheat bran, however, they exerted higher cytotoxic effects on cancer cells than the positive control chlorambucil (IC50 = 58.7 μg/ml). This research suggested that alkylresorcinols are important for the cancer preventive activity of wheat bran. Other lipophilic compounds such as some free unsaturated fatty acids and phytosteroids may also contribute to the anticancer activity.
[show abstract][hide abstract] ABSTRACT: 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.
[show abstract][hide abstract] ABSTRACT: Postprandial hyperglycaemia is a primary risk factor in the development of Type 2 diabetes. α-Glucosidase inhibitors that reduce postprandial hyperglycaemia have a key role in the treatment of Type 2 pre-diabetic states and also have the potential to reduce the progression to complications of diabetes. Epidemiological studies showed that risk for Type 2 diabetes mellitus was decreased with consumption of whole grains. The bran and germ of whole wheat are major components of whole grain consumption and are widely accepted as important ingredients in many low glycaemic index (GI) foods. In this study, the α-glucosidase inhibitory activity of wheat bran and germ was investigated. The active compounds were screened using an in vitro enzyme-inhibitory assay guided fractionation. Potent α-glucosidase inhibitory compounds from wheat germ were identified as phosphatidic acids, 1,2-dilinoleoylglycero-3-phosphate and 1-palmitoyl-2-linoleoyl-glycero-3-phosphate. The low GI property of whole grain wheat could be attributed to these α-glucosidase inhibitory phosphatidic acids, which have the potential to prevent or treat Type 2 diabetes.
[show abstract][hide abstract] ABSTRACT: A detailed investigation of the wood, leaf, branch and root oil of Eremophila mitchellii (Benth.) was carried out by a combination of GC-FID, GC-MS and NMR. The wood oil was composed predominantly of eremophilanes, a rare class of biologically active, bicyclic sesquiterpenoids. The root oil was also found to contain the eremophilanes together with the zizaene sesquiterpene, sesquithuriferone. 9-Hydroxy-1,7(11),9-eremophilatrien-8-one and the known 1(10),11-eremophiladien-9-one (eremophilone), 9-hydroxy-7(11),9-eremophiladien-8-one (2-hydroxyeremophilone), 8-hydroxy-11-eremophilen-9-one (santalcamphor), 8-hydroxy-10,11-eremophiladien-9-one, sesquithuriferone and 8-hydroxy-1,11-eremophiladien-9-one were purified and elucidated by NMR. Three approaches to the purification of the major eremophilanes from the wood oil are described. (+) Spathulenol, α-pinene, globulol, viridiflorene were the major constituents of the leaf oil. All of the essential oils and the eremophilanes exhibited cytotoxicity against P388D(1) mouse lymphoblast cells in-vitro.
[show abstract][hide abstract] ABSTRACT: Bioactivity-guided fractionation of an ethanolic extract of the rhizome of Pleuranthodium racemigerum, a tropical Zingiberaceae species from Northeastern Australia, resulted in the isolation and structural elucidation of 1-(4''-methoxyphenyl)-7-(4'-hydroxyphenyl)-(E)-hept-2-ene (1), a new diarylheptanoid related to curcumin. Compound 1 was a fairly potent inhibitor of prostaglandin E(2) production in 3T3 murine fibroblasts (IC(50) approximately 34 microM) and also displayed moderate cytotoxicity against this cell line (IC(50) = 52.8 microM). The compound also demonstrated cytotoxic activity against the P388D1 murine lymphoblast cell line (IC(50) = 117.0 microM) and four human cell lines: Caco-2 colonic adenocarcinoma (IC(50) = 44.8 microM), PC3 prostate adenocarcinoma (IC(50) = 23.6 microM), HepG2 hepatocyte carcinoma (IC(50) = 40.6 microM), and MCF7 mammary adenocarcinoma (IC(50) = 56.9 microM). The cytotoxicity of compound 1 closely resembled that of curcumin, in terms of both IC(50) values and dose-response curves.
Journal of Natural Products 03/2010; 73(4):743-6. · 3.29 Impact Factor
[show abstract][hide abstract] ABSTRACT: Eleven new bisresorcinols including four mixtures each of two isomers and one resorcinol/phloroglucinol derivative, together with five known resorcinols have been isolated from the ethyl acetate extract of stems of Grevillea whiteana. The new compounds were identified as 4-(3-hydroxy-3-methylbutyl)grebustol-B (10a), 4'-(3-hydroxy-3-methylbutyl)grebustol-B (10b), 4-(4-hydroxy-3-methylbutyl)grebustol-B (2a) and 4'-(4-hydroxy-3-methylbutyl) rebustol-B (2b), 2,2-dimethyldihydropyrano grebustol-B (11a) and iso-2,2-dimethyldihydropyranogrebustol-B (11b), 2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7a) and iso-2,2-dimethyl-3xi-hydroxydihydropyranogrebustol-B (7b), 15-(2-(4-hydroxy-3-methylbutyl)-resorcinol-5-yl)-1-(phloroglucinolyl)-9(Z)pentadecen-one (whiteanone) (4), 5,5'-(hexadecan-diyl)bisresorcinol (12) and 2-methyl-5,5'-(8(Z)-hexadecen-1,16-diyl)bisresorcinol (9). This is the first record of pyranobisresorcinols in the genus and the first report of a phloroglucinol terminal phenolic unit in any Grevillea species.
[show abstract][hide abstract] ABSTRACT: Seven new bisresorcinol derivatives, together with four known resorcinols, have been isolated from the ethyl acetate extract of the stems of Grevillea floribunda. Five of the new compounds (floribol A–E) were characterized as bisnorstriatol derivatives substituted at C-2 of both resorcinol units with variously modified prenyl (3-methylbut-2-enyl) units. The remaining two new compounds are similarly substituted derivatived of grebustol-B.
Centre for Phytochemistry and Pharmacology Papers. 01/2009;