Two New Flavonoids from Retama raetam

Two new furanoflavonoids, retamasins A and B ( 1 and 2 , resp.), along with five known flavonoids, 3 – 7 , were isolated from the aerial parts of Retama raetam. Their structures were determined on the basis of extensive spectroscopic (IR, MS, and 1D‐ and 2D‐NMR) analyses and by comparison with the literature data. This is the first report of the isolation of new furanoflavonoids 1 and 2 from Retama genus, while compounds 3, 5 , and 6 were found for the first time from R. raetam. Antioxidant and anti‐inflammatory activities of the isolated compounds were also evaluated. Compounds 2, 3 , and 5 – 7 exhibited potent inhibitions of iNOS activity with IC₅₀ values of 2.9, 5.0, 3.1, 1.2, and 4.8 μg/ml, respectively. All compounds inhibited NF‐κB except 1 and 5 . Compound 6 was most active in inhibiting iNOS and NF‐κB activity, as well as in decreasing oxidative stress.     

Analysis of essential oils from Voacanga africana seeds at different hydrodistillation extraction stages: chemical composition,antioxidant activity and antimicrobial activity

In this study, essential oils from Voacanga africana seeds at different extraction stages were investigated. In the chemical composition analysis, 27 compounds representing 86.69–95.03% of the total essential oils were identified and quantified. The main constituents in essential oils were terpenoids, alcohols and fatty acids accounting for 15.03–24.36%, 21.57–34.43% and 33.06–57.37%, respectively. Moreover, the analysis also revealed that essential oils from different extraction stages possessed different chemical compositions. In the antioxidant evaluation, all analysed oils showed similar antioxidant behaviours, and the concentrations of essential oils providing 50% inhibition of DPPH-scavenging activity (IC₅₀) were about 25 mg/mL. In the antimicrobial experiments, essential oils from different extraction stages exhibited different antimicrobial activities. The antimicrobial activity of oils was affected by extraction stages. By controlling extraction stages, it is promising to obtain essential oils with desired antimicrobial activities.     

Antibacterial, antifungal and cytotoxic activities of two flavonoids from Retama raetam flowers

We have investigated the antibacterial, antifungal and cytotoxic activities of two flavonoids isolated from Retama raetam flowers using the disc diffusion and micro-dilution broth methods. The cytotoxic activity was tested against Hep-2 cells using the MTT assay. The compounds licoflavone C (1) and derrone (2) were active against Pseudomonas aeruginosa and Escherichia coli (7.81-15.62 μg/mL) and showed important antifungal activity. Strong antifungal activity against Candida species (7.81 μg/mL) was for example found with compound 2. The tested compounds also showed strong cytotoxicity against Hep-2 cells. These two compounds may be interesting antimicrobial agents to be used against infectious diseases caused by many pathogens.     

Chemical composition and antimicrobial activity of essential oils from Centaurea pannonica and C. jacea

The chemical composition and antimicrobial activity of the essential oils obtained by hydrodistillation from Centaurea pannonica (Heufel) Simonkai and C. jacea L. (Asteraceae), were investigated. The essential oils were analyzed by GC and GC-MS. Forty five and twenty nine compounds were identified in the two oils, respectively. C. pannonica oil was rich in fatty acids (43.7%), with 9-octadecanoic acid (34.0%) and (Z,Z)-9,12-octadecadienoic acid (8.6%) as the major compounds. In contrast, the essential oil of C. jacea was dominated by oxygenated sesquiterpenes (43.2%), among which caryophyllene oxide (23.5%) and spathulenol (8.9%) were the major constituents. However, the oil was also characterized by an important fatty acid fraction (15.5%), with 9-octadecanoic acid (8.9%) and hexadecanoic acid (6.6%) being the main components. The antimicrobial activities of the essential oils were evaluated by the microdilution method against three Gram-positive and three Gram-negative bacteria, and one yeast. Both oils exhibited significant antimicrobial activity, especially against Gram-positive bacteria.     

Chemical composition, olfactory evaluation and antimicrobial activity of selected essential oils and absolutes from Morocco

The chemical compositions of selected essential oils from North Africa, especially Morocco, of geranium, wild Moroccan chamomile and rosemary as well as absolutes of rose and geranium were determined using GC/FID and GC/MS. These oils and absolutes were tested concerning their antimicrobial activity against some food spoilage strains obtained from fresh milk and minced meat products, like sausages and pork fillet, in accordance with ISO testing procedures. Gram-positive (Bacillus cereus and Staphylococcus aureus) and Gram-negative (Escherichia coli, Salmonella abony and Pseudomonas aeruginosa) strains were used, as well as the yeast Candida albicans. Using a serial broth dilution method, all samples demonstrated weak antimicrobial activity against the Gram-negative bacteria and the yeast, compared with the activity towards the Gram-positive bacteria.     

Essential oils in combination and their antimicrobial properties

Essential oils (EOs) have been long recognized for their antibacterial, antifungal, antiviral, insecticidal and antioxidant properties. They are widely used in medicine and the food industry for these purposes. The increased interest in alternative natural substances is driving the research community to find new uses and applications of these substances. EOs and their components show promising activities against many food-borne pathogens and spoilage microorganisms when tested in vitro. In food systems, higher concentrations of EOs are needed to exert similar antibacterial effects as those obtained in in vitro assays. The use of combinations of EOs and their isolated components are thus new approaches to increase the efficacy of EOs in foods, taking advantage of their synergistic and additive effects. The purpose of this review is to provide an overview on the antimicrobial efficacy of these combinations. A survey of the methods used for the determination of the interactions and mechanisms involved in the antimicrobial activities of these combinations are also reported.     

Chemical composition and antimicrobial activity of the essential oils from flowers and leaves of Grindelia integrifolia DC

Essential oils from flowers and leaves of Grindelia integrifolia DC. were investigated for the first time in terms of chemical composition and antimicrobial activity. The GC-FID/MS analysis allowed for the identification of 58 and 72 volatiles, comprising 92.4 and 90.1% of the oils, respectively. The major components of the flower oil were α-pinene (34.9%) and limonene (13.1%), while myrcene (16.9%), spathulenol (12.3%), β-eudesmol (11.9%) and limonene (10.1%) dominated among the leaf volatiles. The antimicrobial activity, evaluated against 12 selected bacteria and fungus, was found moderate, with the strongest effect of both oils observed against C. albicans (MIC = MBC: 0.63 and 0.31 mg/mL for flower and leaf oil, respectively).     

Chemical composition and antimicrobial activity of the essential oils of Ferula latisecta and Mozaffariania insignis from Iran

The hydrodistilled oils from the aerial parts of Ferula latisecta and Mozaffariania insignis, which is endemic to Iran, were analyzed by GC and GC/MS. (Z)-Ocimenone (32.4%), (E)-ocimenone (20.3%), and cis-pinocarvone (11.4%) were the main components among the 22 constituents characterized in the oil of F. latisecta, representing 87.7% of the total components detected. Twenty-five compounds were identified in the oil of M. insignis, representing 99.0% of the total oil, with octyl acetate (41.1%), β-pinene (30.3%), and α-pinene (23.9%) as the main constituents. The essential oils were examined for their potential antimicrobial activities. Published in Khimiya Prirodnykh Soedinenii, No. 6, pp. 561–563, November–December, 2006.     

Chemical composition,cytotoxicity, antimicrobial and antifungal activity of several essential oils

Essential oils (EOs) are known and used for their biological, antibacterial, antifungal and antioxidant properties. Numerous studies have shown that EOs exhibit a large spectrum of biological activities in vitro. The incidence of drug-resistant pathogens and the toxicity of antibiotics have drawn attention to the antimicrobial activity of natural products, encouraging the development of alternative treatments. The aim of this study was to analyse the phytochemical and the cytotoxic characteristic of 36 EOs; we then evaluated the antimicrobial activity of the less-toxic EOs on Gram-positive, Gram-negative and fungi strains. The results showed low cytotoxicity in seven EOs and good activity against Gram-negative and Candida spp. strains. Based on our results, EOs could be proposed as a novel group of therapeutic agents. Further experiments are necessary to confirm their pharmacological effectiveness, and to determine potential toxic effects and the mechanism of their activity in in vivo models.     

Essential oils and their constituents: anticonvulsant activity

A literature-based survey of plants species and their essential oils with anticonvulsant activity was carried out. As results, 30 species belonging to 13 families and 23 genera were identified for their activities in the experimental models used for anticonvulsant drug screening. Thirty chemical constituents of essential oils with anticonvulsant properties were described. Information on these 30 species is presented together with isolated bioactive compound studies.     

Chemical composition and antimicrobial activity of some oleogum resin essential oils from Boswellia spp. (Burseraceae)

The chemical composition of Boswellia carteri (Somalia), B. papyrifera (Ethiopia), B. serrata (India) and B. rivae (Ethiopia) oleogum resin essential oils was investigated using GC-MS to identify chemotaxonomy marker components. Total ion current peak areas gave good approximations to relative concentrations based on GC-MS peak areas. B. carteri and B. serrata oleogum resin oils showed similar chemical profiles, with isoincensole and isoincensole acetate as the main diterpenic components. Both n-octanol and n-octyl acetate, along with the diterpenic components incensole and incensole acetate, were the characteristic compounds of B. papyrifera oleogum resin oil. Hydrocarbon and oxygenated monoterpenes were the most abundant classes of compounds identified in the B. rivae oleogum resin oil. The antimicrobial activities of the essential oils were individually evaluated against different microorganisms including fungi, Gram-positive and Gram-negative bacteria strains. The essential oils with the best activity against fungal strains were those obtained from B. carteri and B. papyrifera with MIC values as low as 6.20 microg/ml. The essential oil of B. rivae resin showed the best activity against C. albicans with a MIC value of 2.65 microg/ml.     

Eucalyptus oleosa essential oils: chemical composition and antimicrobial and antioxidant activities of the oils from different plant parts (stems, leaves, flowers and fruits)

Essential oils obtained by hydrodistillation from the different parts (stems, adult leaves, immature flowers and fruits) of Eucalyptus oleosa were screened for their antioxidant and antimicrobial properties and their chemical composition. According to GC-FID and GC-MS, the principal compound of the stem, immature flowers and the fruit oils was 1,8-cineole, representing 31.5%, 47.0% and 29.1%, respectively. Spathulenol (16.1%) and γ-eudesmol (15.0%) were the two principal compounds of adult leaves oil. In the DPPH (1,1-diphenyl-2-picrylhydrazyl) assay, the oils of the four parts showed moderate antioxidant activity. In the ABTS (2,2'-azinobis-3-ethylbenzothiazoline-6-sulphonate) assay, the most active part was the adult leaves, with a IC(50) value 13.0 ± 0.6 mg/L, followed by stems (IC(50) = 43.5 ± 1.4 mg/L). The essential oils showed a better antibacterial activity against Gram-positive and Gram-negative bacteria, and a significant antifungal activity also was observed against yeast-like fungi. A strong correlations between oxygenated monoterpenes and antimicrobial activity (especially 1,8-cineole) were noted (R2 = 0.99, 0.97 and 0.79 for B. subtilis, P. aeruginosa and C. albicans, respectively).     

Essential oil from the leaves of Annona vepretorum: chemical composition and bioactivity

The essential oil from the leaves of Annona vepretorun was obtained by hydrodistillation using a Clevenger-type apparatus and analyzed by GC-MS and GC-FID. Eighteen compounds representing 98.1% of the crude essential oil were identified. The major compounds identified were bicyclogermacrene (43.7%), spathulenol (11.4%), alpha-felandrene (10.0%), alpha-pinene (7.1%), (E)-beta-ocimene (6.8%), germacrene D (5.8%), and p-cymene (4.2%). The trypanocidal activity against Trypanosoma cruzi epimastigote forms, as well as, the antimicrobial and antioxidant proprieties was investigated. The essential oil showed a potent trypanocidal activity with IC50 value of 31.9 +/-1.3 microg x mL(-1). For antimicrobial activity, the best result was observed against Candida tropicalis with a MIC value of 100 microg x mL(-1). For antioxidant capacity the essential oil showed weak activity.     

Seasonal variation in the chemical composition and antimicrobial activity of volatile oils of three species of Leptospermum (Myrtaceae) grown in Brazil

This study investigates the seasonal variation of three species of Leptospermum (Myrtaceae) grown in Brazil. The chemical composition of the volatile oils of L. flavescens and L. petersonii did not show any significant seasonal variation in the major components, while for Leptospermum madidum subsp. sativum the levels of major constituents of the volatile oils varied with the harvest season. Major fluctuations in the composition of L. madidum subsp. sativum oil included α-pinene (0-15.2%), β-pinene (0.3-18.5%), α-humulene (0.8-30%), 1,8-cineole (0.4-7.1%) and E-caryophyllene (0.4-11.9%). Levels of β-pinene (0.3-5.6%), terpinen-4-ol (4.7-7.2%) and nerolidol (55.1-67.6%) fluctuated seasonally in the L. flavescens oil. In L. petersonii, changes were noted for geranial (29.8-32.8%), citronellal (26.5-33.9%) and neral (22.7-23.5%). The activity of the volatile oils against the tested bacteria differed, depending on season the oils were obtained. In general, the volatile oils were more active against Gram-positive bacteria.     

Antifungal activity and chemical composition of essential oils from Smyrnium olusatrum L. (Apiaceae) from Italy and Portugal

The essential oils and supercritical CO? extracts of wild Smyrnium olusatrum L. growing in Sardinia (Italy) and in Portugal were investigated. For the study, oils were isolated from total plant aerial part (umbels containing seeds). The content of β-phellandrene (67.3% vs. 42.7%) and α-pinene (31.9% vs. 1.2%), respectively, the main components of Portuguese and Italian essential oils, declined during the maturation stage of the umbels. Contrarily, some other important components, particularly curzerene, germacrene B, germacrone, alexandrofuran, 1-β-acetoxyfurano-4(15)-eudesmene and 1-β-acetoxyfurano-3-eudesmene, increased in fruiting umbels. The chemical composition of the Sardinian oil is rather different from those of other origin. The composition of the supercritical extracts and the essential oils is markedly different, particularly due to the high amount of furanosesquiterpenoids in the supercritical fluid extraction. The minimal inhibitory concentration (MIC) and the minimal lethal concentration 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 oils were particularly active against dermatophyte strains and C. neoformans, with MIC values in the range of 0.32-0.64?μL?mL?1.     

Salvia officinalis L. essential oils: effect of hydrodistillation time on the chemical composition, antioxidant and antimicrobial activities

Salvia officinalis L. oils were isolated from the plant's commercial dried aerial parts, by hydrodistillation, with different distillation times. The essential oils were analysed by gas chromatography and gas chromatography-mass spectrometry. The antioxidant ability was measured using a free radical scavenging activity assay using 2,2-diphenyl-1-picrylhydrazyl (DPPH), a thiobarbituric acid reactive substances (TBARS) assay, a deoxyribose assay for the scavenging of hydroxyl radical, an assay for site-specific actions and a 5-lipoxygenase assay. Antibacterial activity was determined by the agar diffusion method. 1,8-Cineole, α-pinene and camphor were the dominant components of all the essential oils. The different hydrodistillation times did not affect the oil yield nor the relative amount of the oil components. The time of hydrodistillation influenced the antioxidant activity. With the DPPH method, the oils isolated for 2 and 3 h were stronger free radical scavengers, while with the TBARS method, the highest antioxidant values were obtained in the oils isolated for 30 min, 2 and 3 h. Hydroxyl radical scavenging and lipoxygenase activity assays showed the best results with oils isolated for 1 and 3 h. With the deoxyribose method, sage oils at concentrations <1000 mg L(-1) showed better activity than mannitol. The essential oil of S. officinalis showed very weak antimicrobial activity.     

Bio-Guided Fractionation of Retama raetam (Forssk.) Webb & Berthel Polar Extracts

The fractionation of the methanolic extract (MeOH-E) of Retama raetam (Forssk.) Webb & Berthel and further analysis by thin layer chromatography resulted in four fractions (F1, F2, F3 and F4) that, in parallel with the MeOH-E, were screened for antioxidant, cytotoxic, antidiabetic and antibacterial properties. In addition, chemical characterization of their bioactive molecules was performed using LC-DAD-ESI/MSⁿ. The results indicated that F3 was the most promising regarding antioxidant and cytotoxicity abilities, possibly due to its richness in flavonoids class, particularly isoflavones. In turn, F1 was characterized by the presence of the most polar compounds from MeOH-E (organic acids and piscidic acid) and showed promising abilities to inhibit α-amylase, while F4, which contained prenylated flavonoids and furanoflavonoids, was the most active against the tested bacteria. The gathered results emphasize the distinct biological potentials of purified fractions of Retama raetam.     

Properties and limits of some essential oils: chemical characterisation,antimicrobial activity,interaction with antibiotics and cytotoxicity

Because of the emergence of multi-drug resistance bacteria and fungi, alternatives to conventional antimicrobial therapy are needed. This study aims to evaluate in vitro the antimicrobial activity of: Mirtus communis, Coriandrum sativum, Pelargonium capitatum, Cuminum cyminum, Ocimum basilicum, Citrus aurantium amara, Cymbopogon. winterianus, Cymbopogon martini, Salvia sclarea, Melaleuca alternifolia and Mentha suaveolens essential oils on bacteria and fungi, in relation to their chemical composition. The potential interaction of M. alternifolia (TTO), C. sativum (CDO) and M. suaveolens (EOMS) essential oils when used in combination with gentamicin and fluconazole has been evaluated. The results obtained showed a synergic effect on some bacteria and fungi, with FICI values ≤5. The cytotoxicity of TTO, CDO and EOMS was investigated towards HeLa cells. Only EOMS did not result cytotoxic at the active concentrations on micro-organisms. Further studies are necessary to obtain optimal ratios and dosing regimens for higher therapeutic efficacy and to decrease toxicological profiles.     

Chemical composition and antimicrobial activities of the essential oils from Ocimum selloi and Hesperozygis myrtoides

Ocimum selloi, a traditional medicinal plant from Brazil, is sold in open-air markets at Rio de Janeiro State. Hesperozygis myrtoides is a very aromatic small bush found in the State of Minas Gerais, Brazil, growing at an altitude of 1800m. The chemical composition of both essential oils was analyzed as well as their antimicrobial activity against fungi and bacteria. For all specimens of Ocimum selloi obtained at open-air markets, methylchavicol was major compound found (93.6% to 97.6%) in their essential oils. The major compounds identified in the oil of H. myrtoides were pulegone (44.4%), isomenthone (32.7%), and limonene (3.5%). Both oils displayed antimicrobial activity against all tested microorganisms but Candida albicans was the most susceptible one. Combinations of the two oils in different proportions were tested to verify their antimicrobial effect against C. albicans, which, however, was not modified in any of the concentrations tested. The minimum inhibitory concentration (MIC) was determined to confirm the antimicrobial activity against C. albicans as well as other clinical isolates (C. glabrata, C. krusei, C. parapsilosis and C. tropicalis).