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Chemical composition and in vitro evaluation of antioxidant and antibacterial activities of the root oil of Ridolfia segetum (L.) Moris from Tunisia
Abstract
The present work describes the chemical composition and evaluates the antibacterial and the antioxidant properties of root oil from Ridolfia segetum, a traditional medicinal plant widely distributed in Tunisia. The essential oil, analysed by combination of GC, GC/MS and (13)C-NMR, was dominated by dillapiole (47.4%) and myristicin (19.2%). The antioxidant potential of the essential oil was evaluated using the 2,2'-diphenyl-1-picrylhydrazyl free radical scavenging method. The phenylpropanoid-rich root oil possesses good antioxidant properties (IC(50) = 38 mg mL(-1)). The essential oil was evaluated for its antibacterial activity using the microdilution assay, resulting in the inhibition of a number of common human pathogenic bacteria as well as of some clinical and environmental isolated strains. The minimum inhibitory concentrations of the essential oil varied between 1.25 and 5 mg mL(-1) and the minimum bactericidal concentrations were superior to 5 mg mL(-1) of oil for most strains. These results may suggest that the root oil of R. segetum possesses compounds with antibacterial and antioxidant capacities, and therefore can be explored as a natural preservative ingredient in food and/or for pharmaceutical preparations.
... The antibacterial activity of essential oils is mainly a function of their chemical composition; in particular, their major volatile compounds [41]. Due to the variability of the components of essential oils, it is likely that their antimicrobial activity is not attributable to a single mechanism, but to several sites of action at the cellular level [13]. ...
... Due to the variability of the components of essential oils, it is likely that their antimicrobial activity is not attributable to a single mechanism, but to several sites of action at the cellular level [13]. The mode of action of essential oils depends primarily on the type of the characteristics of the active components, in particular their hydrophobic property which allows them to penetrate the phospholipid double layer of the bacterial [13,41]. The membrane of the bacterial cell induce a change in membrane conformation, a chelo-osmotic disturbance and an ion leak (K+): this mechanism was observed with tea tree oil on the bacteria Gram+ and Gram-, and yeast under in vitro conditions. ...
... In general, Gram-bacteria are more resistant than Gram+ thanks to the structure of their external membrane. Antibiotic targets are involved in the physiological or metabolic functions of the bacteria [4,13,41,42]. Badawy and Abdelgaleil [43] showed that the essential oil of Thuja occidentalis revealed the highest antibacterial activity among the eighteen tested essential oils on Agrobacterium tumefaciens and Erwinia carotovora var. carotovora. ...
Recently plant essential oils received increasing attention for plant health and food security in the sustainable agriculture context. Essential oils are promising biological sources since they are cost-effective, biodegradable, and safe for human health and the environment. This review covers the essential extraction characteristic, extraction methods, and conservation needed for the scientist's and industries' knowledge. Furthermore, the main biological activities and involvement of essential oils in plant pests and diseases are outlined. Finally, this review concludes the potential commercial application and the future challenges of essential oils as an eco-friendly method in sustainable agriculture.
... The antibacterial activity of essential oils is mainly a function of their chemical composition; in particular, their major volatile compounds [41]. Due to the variability of the components of essential oils, it is likely that their antimicrobial activity is not attributable to a single mechanism, but to several sites of action at the cellular level [13]. ...
... Due to the variability of the components of essential oils, it is likely that their antimicrobial activity is not attributable to a single mechanism, but to several sites of action at the cellular level [13]. The mode of action of essential oils depends primarily on the type of the characteristics of the active components, in particular their hydrophobic property which allows them to penetrate the phospholipid double layer of the bacterial [13,41]. The membrane of the bacterial cell induce a change in membrane conformation, a chelo-osmotic disturbance and an ion leak (K+): this mechanism was observed with tea tree oil on the bacteria Gram+ and Gram-, and yeast under in vitro conditions. ...
... In general, Gram-bacteria are more resistant than Gram+ thanks to the structure of their external membrane. Antibiotic targets are involved in the physiological or metabolic functions of the bacteria [4,13,41,42]. Badawy and Abdelgaleil [43] showed that the essential oil of Thuja occidentalis revealed the highest antibacterial activity among the eighteen tested essential oils on Agrobacterium tumefaciens and Erwinia carotovora var. carotovora. ...
Recently plant essential oils received increasing attention for plant health and food security in the sustainable agriculture context. Essential oils are promising biological sources since they are cost-effective, biodegradable, and safe for human health and the environment. This review covers the essential extraction characteristic, extraction methods, and conservation needed for the scientist’s and industries’ knowledge. Furthermore, the main biological activities and involvement of essential oils in plant pests and diseases are outlined. Finally, this review concludes the potential commercial application and the future challenges of essential oils as an eco-friendly method in sustainable agriculture.
... Traditional medicine makes extensive use of Moris for treating a broad variety of illnesses, including: cough, constipation, respiratory tract infections, and stomach acidity. [4][5][6]. It regulates menstruation in women and increases milk production in nursing mothers, the infusion of grains helps to fight against constipation and intestinal gas [7]. ...
... The ethnobotanical studies in Morocco have indicated the traditional use of R. segetum (L.) Moris as an antidiabetic plant [9][10][11]. The frequent use of this species in traditional medicine and the confirmation of its effectiveness by scientific laboratory studies have led to the identification of its various biological properties such as antioxidant activity [5,6], antibacterial [6,[12][13][14], anti-inflammatory [5], anticancer [15,16], HIV-1 inhibition [4] and insecticidal activity [14,17]. Diabetes mellitus is defined by persistent hyperglycemia, which affects carbohydrate, lipid, and protein metabolism and comes from a deficiency in the production of insulin, the action of insulin, or both conjugates. ...
... The ethnobotanical studies in Morocco have indicated the traditional use of R. segetum (L.) Moris as an antidiabetic plant [9][10][11]. The frequent use of this species in traditional medicine and the confirmation of its effectiveness by scientific laboratory studies have led to the identification of its various biological properties such as antioxidant activity [5,6], antibacterial [6,[12][13][14], anti-inflammatory [5], anticancer [15,16], HIV-1 inhibition [4] and insecticidal activity [14,17]. Diabetes mellitus is defined by persistent hyperglycemia, which affects carbohydrate, lipid, and protein metabolism and comes from a deficiency in the production of insulin, the action of insulin, or both conjugates. ...
The present work was designed to study the chemical composition, antioxidant, antihyperglycemic effect, and toxicity assessment of Ridolfia segetum (L.) Moris extract. The chemical composition was studied by use of high-performance liquid chromatography (HPLC). Antioxidant power was tested by use of DPPH and FRAP assays. The antihyperglycemic effect was tested by use of a glucose tolerance test, while toxicity assessment was done in vivo by use of Wistar rats for 14 days. Analysis of the extract by HPLC-UV revealed the presence of gallic acid, catechol, vanillic acid, catechin, tannic acid, rosmarinic acid, naringenin, and coumarin acid. The crude hydroethanolic extract possessed high levels of total phenols (15.6 ± 1.76 mg EAG/g), condensed tannins (383.49 mg ECat/g DM), and flavonoid (11.63 mg EQ/g). The findings showed that the studied extract possessed good antioxidant power with IC50 values equal to 550, 650, 700 µg/mL respectively for the decoction, the ethyl acetate fraction (F2M), and the ethyl acetate fraction (F2E). For the antioxidant activity by FRAP, the aqueous fraction (F3E) and the aqueous extract (F4) showed CE50 values of 0.33 mg/mL and 0.4 mg/mL, respectively. Glucose tolerance test analysis showed that R. segetum (L.) Moris decoction had a significant postprandial antihyperglycemic effect in normal Wistar rats. The results of the acute toxicity test showed that the decoction was not toxic even at 2 g/Kg. Pancreatic α-amylase activity was significantly inhibited in the presence of R. segetum (L.) Moris extract (IC50 = 0.133 ± 0.09 mg/mL). The outcome of the present work showed that R. segetum (L.) Moris is very rich in phenolic compounds with potent antioxidant and antihyperglycemic effects.
... R. segetum is an annual plant widely distributed throughout the Mediterranean basin in areas such as Morocco (Gattefossé and Igolen 1946), Tunisia (Jabrane et al. 2010), Portugal (Cabral et al. 2015), Sardinia (Marongiu et al. 2007), Spain and the Canaries (Palá-Paúl et al. 2002), where it grows as a weed in cereal fields (Pottier-Alapetite 1979). It is used in traditional medicine to prevent coughing, constipation, respiratory tract infections and for treatment of gastric acidity (Cabral et al. 2015). ...
... Chemical characterization of the essential oil (EO) has been reported for the ecotypes of R. segetum grown in different countries and in different localities of the same country, enabling the recognition of two types of oils: those dominated by monoterpene hydrocarbons: α-phellandrene, terpinolene and p-cymene (Palá-Paúl et al. 2002, 2005Marongiu et al. 2007;Bicchi et al. 2009;Jabrane et al. 2009;Poças et al. 2014;Cabral et al. 2015), and those which also contain phenylpropanoids (typically myristicin and dillapiol) as major compounds (Gattefossé and Igolen 1946;Gattefosse and Igolen 1951;Palá-Paúl et al. 2002, 2005Jannet and Mighri 2007;Marongiu et al. 2007;Jabrane et al. 2010;El Karkouri et al. 2017). Biological activities of R. segetum EO include antioxidant (Jabrane et al. 2010;Cabral et al. 2015), antibacterial (Jannet and Mighri 2007;Jabrane et al. 2009), insecticidal (Badalamenti et al. 2021, anti-inflammatory (Cabral et al. 2015), anticancer (Poças et al. 2014) and HIV-1-inhibiting activities (Bicchi et al. 2009). ...
... Chemical characterization of the essential oil (EO) has been reported for the ecotypes of R. segetum grown in different countries and in different localities of the same country, enabling the recognition of two types of oils: those dominated by monoterpene hydrocarbons: α-phellandrene, terpinolene and p-cymene (Palá-Paúl et al. 2002, 2005Marongiu et al. 2007;Bicchi et al. 2009;Jabrane et al. 2009;Poças et al. 2014;Cabral et al. 2015), and those which also contain phenylpropanoids (typically myristicin and dillapiol) as major compounds (Gattefossé and Igolen 1946;Gattefosse and Igolen 1951;Palá-Paúl et al. 2002, 2005Jannet and Mighri 2007;Marongiu et al. 2007;Jabrane et al. 2010;El Karkouri et al. 2017). Biological activities of R. segetum EO include antioxidant (Jabrane et al. 2010;Cabral et al. 2015), antibacterial (Jannet and Mighri 2007;Jabrane et al. 2009), insecticidal (Badalamenti et al. 2021, anti-inflammatory (Cabral et al. 2015), anticancer (Poças et al. 2014) and HIV-1-inhibiting activities (Bicchi et al. 2009). The efficacy of the EO as a biopesticide against plant pathogens and pests has not been reported. ...
The present study characterized and evaluated the antifungal, nematicidal, acaricidal and repellent activities of Ridolfia segetum essential oil (EO), against the fungus Botrytis cinerea Pers., the nematode Meloidogyne javanica and the mite Tetranychus urticae Koch under laboratory conditions. The EO exerted inhibition of the mycelial growth of B. cinerea with median inhibitory concentration (IC50) of 3.63 μL/mL and 0.92 μL/mL air, under contact and vapor phase conditions, respectively. EO application against M. javanica revealed a strong nematostatic effect on second-stage juveniles (J2) and eggs of the root knot nematode with median lethal concentration (LC50) of 10.37 and 9.26 μL/mL, respectively. The oil was toxic to T. urticae by residual contact with median lethal dose (LD50) of 6005 µL/L and exhibited a repellent effect with a repellency index (RI) of 55%. Results suggest that R. segetum oil has potential to be formulated in biopesticides to control the targeted pest and diseases.
... R. segetum is an annual plant widely distributed throughout the Mediterranean basin in areas such as Morocco (Gattefossé and Igolen 1946), Tunisia (Jabrane et al. 2010), Portugal (Cabral et al. 2015), Sardinia (Marongiu et al. 2007), Spain and the Canaries (Palá-Paúl et al. 2002), where it grows as a weed in cereal fields (Pottier-Alapetite 1979). It is used in traditional medicine to prevent coughing, constipation, respiratory tract infections and for treatment of gastric acidity (Cabral et al. 2015). ...
... Chemical characterization of the essential oil (EO) has been reported for the ecotypes of R. segetum grown in different countries and in different localities of the same country, enabling the recognition of two types of oils: those dominated by monoterpene hydrocarbons: α-phellandrene, terpinolene and p-cymene (Palá-Paúl et al. 2002, 2005Marongiu et al. 2007;Bicchi et al. 2009;Jabrane et al. 2009;Poças et al. 2014;Cabral et al. 2015), and those which also contain phenylpropanoids (typically myristicin and dillapiol) as major compounds (Gattefossé and Igolen 1946;Gattefosse and Igolen 1951;Palá-Paúl et al. 2002, 2005Jannet and Mighri 2007;Marongiu et al. 2007;Jabrane et al. 2010;El Karkouri et al. 2017). Biological activities of R. segetum EO include antioxidant (Jabrane et al. 2010;Cabral et al. 2015), antibacterial (Jannet and Mighri 2007;Jabrane et al. 2009), insecticidal (Badalamenti et al. 2021, anti-inflammatory (Cabral et al. 2015), anticancer (Poças et al. 2014) and HIV-1-inhibiting activities (Bicchi et al. 2009). ...
... Chemical characterization of the essential oil (EO) has been reported for the ecotypes of R. segetum grown in different countries and in different localities of the same country, enabling the recognition of two types of oils: those dominated by monoterpene hydrocarbons: α-phellandrene, terpinolene and p-cymene (Palá-Paúl et al. 2002, 2005Marongiu et al. 2007;Bicchi et al. 2009;Jabrane et al. 2009;Poças et al. 2014;Cabral et al. 2015), and those which also contain phenylpropanoids (typically myristicin and dillapiol) as major compounds (Gattefossé and Igolen 1946;Gattefosse and Igolen 1951;Palá-Paúl et al. 2002, 2005Jannet and Mighri 2007;Marongiu et al. 2007;Jabrane et al. 2010;El Karkouri et al. 2017). Biological activities of R. segetum EO include antioxidant (Jabrane et al. 2010;Cabral et al. 2015), antibacterial (Jannet and Mighri 2007;Jabrane et al. 2009), insecticidal (Badalamenti et al. 2021, anti-inflammatory (Cabral et al. 2015), anticancer (Poças et al. 2014) and HIV-1-inhibiting activities (Bicchi et al. 2009). The efficacy of the EO as a biopesticide against plant pathogens and pests has not been reported. ...
Chemical profiles of essential oils hydrodistilled from whole plants of Senecio glaucus ssp. coronopifolius (Maire) Alexander and aerial parts of Ridolfia segetum (L.) Moris growing in Morocco were determined using gas chromatography/mass spectrometry (GC/MS). The analysis identified 84 compounds in the oil isolated from S. glaucus ssp. coronopifolius and 61 constituents in R. segetum oil. Both oils had a predominance of monoterpene hydrocarbons. α-Pinene (26.2 %) was the main compound of S. glaucus ssp. coronopifolius oil, followed by myrcene (11.4 %) and p-cymene (9.9 %). Novelly (Z)-β-ocimene (19.7 %) dominated R. segetum oil, followed by β-phellandrene (9.6 %) and β-pinene (8.6 %). This is the first report of (Z)-β-ocimene-rich essential oil from R. segetum and α-pinene-rich essential oil from S. glaucus ssp. coronopifolius, revealing new chemical profiles for both species. The oils have potential in agroecological and pharmaceutical formulations, serving both economic and medicinal applications.
... Ridolfia segetum (L.) Moris (R. segetum) belongs to Apiaceae family, being widely distributed along the Mediterranean region (Cabral et al., 2015;Jabrane et al., 2010;Jannet and Mighri, 2007). This plant is already used in traditional medicine to treat gastric acidity and digestive problems, as well as, to prevent infections on the respiratory tract (Bicchi et al., 2009;Cabral et al., 2015;Jabrane et al., 2010). ...
... Ridolfia segetum (L.) Moris (R. segetum) belongs to Apiaceae family, being widely distributed along the Mediterranean region (Cabral et al., 2015;Jabrane et al., 2010;Jannet and Mighri, 2007). This plant is already used in traditional medicine to treat gastric acidity and digestive problems, as well as, to prevent infections on the respiratory tract (Bicchi et al., 2009;Cabral et al., 2015;Jabrane et al., 2010). ...
... Previous studies acknowledged two types of EOs extracted from R. segetum, with a distinct chemical composition, from samples collected from different regions and/or seasons. Therefore, an EO was identified, mainly constituted by monoterpenes hydrocarbons, like α-phellandrene and terpinolene, which is distinguishable from those containing myristicin and dillapiole (phenylpropanoids) as major components (Cabral et al., 2015;Jabrane et al, 2009Jabrane et al, , 2010Jannet and Mighri, 2007;Palá-Paúl et al., 2005). It was previously published, by various studies, the therapeutic potential of R. segetum EO as an anti-inflammatory, antioxidant, and antiviral agent (Bicchi et al., 2009;Cabral et al., 2015;Jabrane et al., 2010;Marongiu et al., 2007). ...
Ethnopharmacological relevance: The past few years have witnessed an increasing interest in essential oils (EOs) as potential therapeutic agents against a wide variety of pathologies, including cancer. EOs extracted from Ridolfia segetum (L.) Moris (R. segetum) are a clear example of a phytoproduct with therapeutic applications, as it is widely used in traditional medicine due to its antioxidant and anti-inflammatory properties, and these properties were already validated by previous studies. Although, it is well established that inflammation is a key hallmark of cancer, with a key role promoting tumorigenesis, and being chronic inflammation often associated with tumorigenic processes, there are no previous studies regarding the assessment of the antitumoural potential of R. segetum EOs.
Aim of the study: The present study intends to be the first to evaluate the antitumoural proprieties of R. segetum EO phytoproducts in cancer cell models.
Materials and Methods: For this, R. segetum EOs were extracted from plants collected at either flowering (RS_Fl) or fruiting (RS_Fr) stage. The impact on proliferation and viability of treatment with R. segetum EO extracts was assessed using in vitro 2D and 3D models.
Results: Both R. segetum EOs presented effective antiproliferative/viability effects, evidence noted by low IC50 values in 2D models, and significant reduction of spheroid size in 3D in vitro models. Mechanistically, treatment with R. segetum EOs was associated with an altered G1 (associated with p21 stabilisation), and subsequent induction of apoptosis.
Conclusions: Overall, these results indicate that R. segetum EOs have potential as suitable antitumoural therapeutic agents.
... The EO of the flowers collected in Portugal showed anti-inflammatory and antioxidant activities [30] and, recently, strong antitumor potential with high capability to inhibit proliferation and induce apoptosis [31]. Jabrane et al. [32,33] and Ben Jannet and Mighri [34] showed the antibacterial activities of the EOs from plants collected in Tunisia, whereas the EO from the Sardinian population was shown to inhibit HIV-1 RT RDDP activity in a dose-dependent manner [35]. ...
... Based on composition of EOs of different accessions of R. segetum studied so far, it is possible to identify three distinct chemotypes: the first one is largely dominated by monoterpene hydrocarbons, usually α-phellandrene, terpinolene, and p-cymene [35,[58][59][60]; a second one which contains phenylpropanoids, usually myristicin and/or dillapiol as major compounds [33,34,61]; and a third one rich in dillapiole and o-cymene [62]. ...
Several species of the family Apiaceae are aromatic herbs that produce essential oils usable on an industrial scale for pharmaceutical, cosmetic, and food purposes. In particular, some essential oils, such as green insecticides for example, may replace synthetic insecticides, keeping most of their efficacy and avoiding environmental pollution or human poisoning. In the present study, we explored the insecticidal potential of Ridolfia segetum (L.) Moris essential oil (EO) against three different pests: Culex quinquefasciatus Say, Musca domestica L., and Spodoptera littoralis (Boisduval). For this purpose, the EO was obtained by hydrodistillation of flowers and its composition was achieved by gas chromatography/flame ionization detection (GC/FID) and gas chromatography/mass spectrometry (GC/MS). This EO was rich in α-phellandrene (49.3%), β-phellandrene (9.2%), terpinolene (20.7%), and piperitenone oxide (5.9%). Concerning the mosquitocidal efficacy, the EO showed noteworthy toxicity against C. quinquefasciatus 3rd instar larvae, with a LC50 = 27.1 µL L−1 and LC90 = 42.5 µL L−1. Regarding M. domestica, a different toxicity of the R. segetum EO was found on male and female flies, calculating LD50 values of 10.5 and 50.8 µg adult−1, respectively. The EO was also toxic to S. littoralis 3rd instar larvae, achieving LD50 and LD90 values of 37.9 and 99.6 µg larva−1, respectively. Overall, this flower EO, extracted from a traditional Sicilian food plant, merits further investigation for the development of green insecticide formulations to be used in real world conditions, pending a careful assessment of non-target toxicity on beneficial organisms.
... Recent studies have focused on the activity of non-nutritional dietary compounds that have protective or disease preventive properties (14)(15)(16). Myristicin (Myr; 1-allyl-5-methoxy-3,4-methylenedioxybenzene) is an active aromatic compound present in nutmeg (the seed of Myristica fragrans), carrot, basil, cinnamon and parsley (15). Myr has been revealed to have antibacterial (16), hepatoprotective (17), anti-inflammatory (18) and anticancer (15) effects. ...
... Myristicin (Myr; 1-allyl-5-methoxy-3,4-methylenedioxybenzene) is an active aromatic compound present in nutmeg (the seed of Myristica fragrans), carrot, basil, cinnamon and parsley (15). Myr has been revealed to have antibacterial (16), hepatoprotective (17), anti-inflammatory (18) and anticancer (15) effects. Additionally, Myr has exhibited significant effects on the CNS. ...
The aim of the present study was to investigate the role of myristicin (Myr; 1‑allyl‑5‑methoxy‑3,4‑methylenedioxybenzene), an active aromatic compound isolated from nutmeg, carrot, basil, cinnamon and parsley, in hypoxia‑induced apoptosis in rat dorsal root ganglion (DRG) neurons. It was observed that Myr significantly enhanced cell viability in hypoxia‑induced DRG neurons in a dose‑dependent manner; the optimal concentration of Myr was 50 µM. Furthermore, Myr reduced the percentage of deoxynucleotidyl transferase‑mediated dUTP nick end‑labeling‑positive neuronal cells and influenced the expression of the pro‑apoptotic gene B‑cell lymphoma 2 (Bcl‑2) associated X protein, the apoptosis protease cleaved caspase‑3 and the anti‑apoptotic gene Bcl‑2, in the hypoxia‑induced group. In addition, Myr protected against hypoxic injury in DRG neurons by inhibiting malondialdehyde and lactate dehydrogenase, however upregulating superoxide dismutase and glutathione peroxidase. Myr reduced the expression of endoplasmic reticulum stress (ERS) markers, including CCAAT/enhancer‑binding protein‑homologous protein, glucose‑related protein 78 and cleaved caspase‑12 in the hypoxia‑induced group. To the best of our knowledge, this is the first demonstration of the activity of Myr against hypoxia‑induced apoptosis in rat DRG neurons via inhibition of the ERS pathway.
... The minimum inhibitory concentrations (MICs) were evaluated according to the reported procedure [29,30] with minor modifications. Briefly, Stenotrophomonas maltophilia ATCC 13637 was cultured on 0002 medium (1% peptone, 0.3% beef extract, and 0.5% NaCl in distilled water with pH 7.0) at 30 • C and prepared for its suspension with a final concentration of 5 × 10 5 CFU/mL. ...
Three new compounds including a meroterpenoid (1) and two isocoumarins (8 and 9), together with thirteen known compounds (2–7, 10–16) were isolated from the metabolites of Talaromyces amestolkiae MST1-15. Their structures were identified by a combination of spectroscopic analysis. The absolute configuration of compound 1 was elucidated on the basis of experimental and electronic circular dichroism calculation, and compounds 8 and 9 were determined by Mo2(OAc)4-induced circular dichroism experiments. Compounds 7–16 showed weak antibacterial activities against Stenotrophomonas maltophilia with MIC values ranging from 128 to 512 μg/mL (MICs of ceftriaxone sodium and levofloxacin were 128 and 0.25 μg/mL, respectively).
... Myristicin is naturally derived from the seeds of the plant Myristica fragrans. Myristicin exhibits anti-inflammatory, antibacterial, anticancer, and hepatoprotective properties (Jabrane et al., 2010;Lee and Park, 2011;Martins et al., 2014;Morita et al., 2003). Myristicin (50 µM) has a neuroprotective effect in hypoxia-treated rat dorsal root ganglion (DRG) neurons by downregulating the expression levels of GRP78, CHOP, and caspase-12 proteins . ...
The primary aim of this review is to summarize the literature on natural products that are effective in the treatment of various neurological disorders by targeting endoplasmic reticulum stress (ERS). Various electronic databases such as SCOPUS, PubMed, Web of Science, and Google Scholar were searched for relevant publications. ERS has been implicated in the pathogenesis of numerous neurological disorders such as cerebral ischemia, Parkinson's disease, Alzheimer's disease, and Huntington’s disease. Several natural products targeting ERS signalling pathways provide therapeutic options for neurological diseases, and in this review, the potential neuroprotective properties of these products are discussed.
... The minimum bactericidal concentrations (MBCs) were determined based on the MIC results [26][27][28]: serial sub-cultivation of a 5 lL aliquot near the MIC in microtiter plates containing 195 lL of Mueller Hinton broth per well; incubation for another 24 h at 37°C. The lowest concentration of antimicrobial agent that killed at least 99.9% of the starting inoculum was defined as the MBC endpoint, which was determined as the lowest concentration with no visible growth by measuring the absorbance at 600 nm using a Multimodel Plate Reader (Infinite 200). ...
Hydrogels are kinds of soft materials with 3D network structure, which play important roles in medical materials, such as contact lenses, surgical implants, wound dressings, artificial skin, drug release carriers, suture coatings, especially antibacterial materials that could solve problems of microbial infections. There are many studies on 18β-glycyrrhetinic acid (GA) derivatives hydrogel, but few on application in antibacterial materials. GA-O-20, one of GA derivatives, showed marvelous antibacterial property compared with its parent compound GA. Therefore, it was adopted as basic functional material to prepare supramolecular self-assembly hydrogels in the mixture solvent of water and ethanol. This hydrogel exhibits outstanding thermodynamic stability; the gel melting temperature (Tgel) is high to 96.6 ± 0.48 °C. Besides, it presented exceptional antibacterial that its minimal inhibitory concentration (MIC) and the minimal bactericidal concentration (MBC) value are 6.25 and 12.5 μM, respectively, which was possibility caused by its sustained self-released property. This supramolecular self-assembly hydrogel may have enormous potentials in the application of antibacterial materials and drug delivery, which can be helpful to expand the application of GA derivatives.
Graphical abstract
... The minimum bactericidal concentrations (MBCs) were determined based on the MIC results (Jabrane et al., 2010;Chouaib et al., 2015;Wu et al., 2018;Wu et al., 2021): serial sub-cultivation of a 5 μL aliquots near the MIC with 195 μL fresh MHB were uniformly inoculated onto MHA solidified in 90 mm Petri dishes; incubation for 24 h at 37°C. The lowest concentration of antimicrobial agent that killed at least 99.9% of the starting inoculum was defined as the MBC endpoint, which was determined as the lowest concentration with no visible growth of bacterial colony on the Petri dishes (Wu et al., 2021). ...
Two essential oils were isolated from discarded perfume lemon and leaves (Citrus limon (L.) Burm. F.) by hydro-distillation with good yield (0.044% for perfume lemon and 0.338% for leaves). Their biological activities were evaluated against five selected bacterial strains and Aedes albopictus (Ae. albopictus, Diptera: Culicidae). Chemical composition indicated that both essential oils were rich in essential phytochemicals including hydrocarbons, monoterpenes and sesquiterpene. These constituents revealed some variability among the oils displaying interesting chemotypes (R)-(+)-limonene (12.29–49.63%), citronellal (5.37–78.70%) and citronellol (2.98–7.18%). The biological assessments proved that the two essential oils had similar effect against bacterial (inhibition zones diameter ranging from 7.27 ± 0.06 to 10.37 ± 0.15 mm; MICs and MBCs ranging from 1.6 to 6.4 mg/mL); against Ae. albopictus larvae (LC50 ranging from 384.81 to 395.09 ppm) and adult mosquito (LD50 ranging from 133.059 to 218.962 μg/cm²); the activity of the two chemotypes ((R)-(+)-limonene and citronellal): larvae (LC50 ranging from 267.08 to 295.28 ppm), which were all presented in dose-dependent manners. Through this work, we have showcased that recycling and reusing of agriculture by-products, such as discarded perfume lemon and leaves can produce eco-friendly alternatives in bacterial disinfectants and mosquito control product.
... The minimal inhibition concentration (MIC) values for the antibacterial activity of the REO and its fractions (R 1 -R 10 ) were assayed by application of the micro-well dilution method described by Jabrane et al. (2010). ...
The aim of this study was to characterize the chemical composition of the roots essential oil from Inula viscosa (L.) through its fractionation during extraction, and to evaluate the antibacterial, anticholinesterase, anti-tyrosinase and anti-5-lipoxygenase activities of the isolated oil (REO) and its fractions (R1–R10). The REO and its fractions (R1–R10) were isolated by hydrodistillation of the fresh roots in a Clevenger type apparatus. Fifty-three constituents were identified by GC-FID and GC–MS analyses. The REO was characterized by a high proportion of oxygenated monoterpenes (50.5%), followed by oxygenated sesquiterpenes (37.5%) and sesquiterpene hydrocarbons (7.6%). The major constituents of the REO and all the fractions were (Z)-neryl isovalerate (17.5–29.8%), 1,10-di-epi-cubenol (19.1–27.2%) and 2,5-dimethoxy-p-cymene (5.9–17.7%). The antibacterial activity of REO and its fractions (R1–R10) was tested by using the micro dilution methods against two Gram-positive and four Gram-negative bacteria. The REO and its fractions (R1–R10) showed a strong inhibition of Enterococcus faecalis (MIC = 20.0 μg/mL) and Staphylococcus aureus (MIC = 20.0 μg/mL). Results showed that the fraction R8 exerted the highest anti-tyrosinase activity, with 88.4% of inhibition at 50 μg/mL, and R1 exhibited a significant 5-lipoxygenase inhibitory effect (IC50 = 21.15 ± 0.12 μg/mL).
... The minimal inhibition concentration (MIC) values for the antibacterial activity were determined with the dilution method following the procedure described by Jabrane et al. [43] The LEO, its volatile fractions (V 1 -V 10 ) and compound 1 were prepared at a concentration of 10 mg/mL by dissolution of the oils in 10 % DMSO. Sterile 10 % DMSO solution (100 μL) was pipetted into all wells of the microtiter plate before transferring 100 μL of stock solution to the microplate. ...
... The minimal inhibition concentration (MIC) values for the antibacterial activity were determined with the dilution method following the procedure described by Jabrane et al. [43] The LEO, its volatile fractions (V 1 -V 10 ) and compound 1 were prepared at a concentration of 10 mg/mL by dissolution of the oils in 10 % DMSO. Sterile 10 % DMSO solution (100 μL) was pipetted into all wells of the microtiter plate before transferring 100 μL of stock solution to the microplate. ...
The chemical composition of the essential oil (LEO) and its volatile fractions (V1–V10) collected during the hydrodistillation process every 15 min from the fresh leaves of I. viscosa (L.), growing in Tunisia, were analyzed by GC‐FID and GC/MS. Eighty‐two compounds, representing 90.9–99.4 % of the total samples, were identified. The crude essential oil (LEO) and its fractions (V1–V10) were characterized by the presence of a high amount of oxygenated sesquiterpenes (82.7–95.8 %). Isocostic acid (1) was found to be the most abundant component (37.4–83.9 %) and was isolated from the same essential oil over silica gel column chromatography and identified by spectroscopic methods (1H, 13C, DEPT 135 NMR and EI‐MS) and by comparison with literature data. Furthermore, the fresh leaves essential oil (LEO), its volatile fractions (V1–V10) as well as compound 1 were screened for their antibacterial, antityrosinase, anticholinesterase and anti‐5‐lipoxygenase activities. It was found that the isolated compound 1 exhibited an interesting antibacterial activity against Staphylococcus aureus ATCC 25923 (MIC=32 μg/mL) and Enterococcus faecalis ATCC 29212 (MIC=32 μg/mL) and the highest antityrosinase activity (IC50=13.82±0.87 μg/mL). Compound 1 was also found to be able to strongly inhibit 5‐lipoxygenase with an IC50 value of 59.21±0.85 μg/mL. The bioactivity and drug likeness scores of compound 1 were calculated using Molinspiration software and interpreted, and the structure‐activity relationship (SAR) was discussed with the help of molecular docking analysis.
... The essential oil of Ridofolia segetum has been the main topic of many studies, based on the quantification of the main compounds of essential oils, chemical characterization studies, allowed the distinction of two types of HE; One is largely dominated by monoterpene hydrocarbons such as α-phelandrene, terpinolene and p-cymene (Bicchi and al., 2009, Fleisher and Fleisher, 1996, Marongiu and al., 2007, Palá-Paúl and al ., 2002; And the one which contains phenylpropanoids as main compounds or in large amounts, generally myristicin and dillapiol (Jannet and Mighri, 2007;Jabrane and al., 2010). The botanical identification of the species was carried out at the laboratory of Floristics of the Scientific Institute in Rabat. ...
... The MIC was defined as the lowest concentration able to inhibit any visible bacterial growth. MIC values were determined by a microtiter plate dilution method Jabrane et al. (2010b) dissolving the sample in 10 % DMSO solution. Sterile 10 % DMSO solution (100 lL) was pipette into all wells of the micro-titer plate before transferring 100 lL of stock solution to the microplate. ...
The essential oils obtained by the hydrodistillation from the fresh flowers, leaves, stems, and roots of Ferula communis L., growing in Tunisia were analyzed by GC and GC/MS. Thirty-two components were identified in the oil of flowers with camphor (18.3 %), α-pinene (15.3 %), and β-eudesmol (9.3 %) as the main constituents. Twenty-nine compounds were identified in the oil of stems with β-eudesmol (28.1 %), δ-eudesmol (11.1 %), and α-eudesmol (9.6 %) as the main compounds. Twenty compounds were characterized in the oil of roots with dillapiole (7.9 %), guaiol (7.3 %), and spathulenol (6.8 %). In the oil of leaves, α-eudesmol (25.2 %), β-eudesmol (20.7 %), δ-eudesmol (10.1 %), and caryophyllene oxide (7.2 %) were found as the main constituents. This study was undertaken to evaluate the antioxidant activity using DPPH (2,2′-diphenyl-1-picrylhydrazyl), ABTS (2,2′-azinobis-3-ethylbenzothiazoline-6-sulfonic acid), reducing power, and catalase activity. We tested also the antibacterial, cytotoxic, and cholinesterase inhibition properties of the essential oil of different organs of F. communis. The essential oil of the stems showed the highest antioxidant activity (IC50 = 0.03 ± 0.001 mg mL−1), in DPPH assay and the important result of catalase (303.03 µmol H2O2 degraded/min/protein) of F. communis. The antibacterial activity of the oil was determined by micro-well dilution assay. The best results (MIC = 0.156 ± 0.02 mg mL−1) were exhibited by the essential oil of the leaves of F. Communis against Pseudomonas aeruginosa. Besides, the strongest cytotoxic activity against Hela cells was shown with essential oils’ leaves with an inhibition percentage of 79.05 % at the concentration of 500 µg mL−1. However, the best inhibition percentage of A 549 cells was detected for essential oils’ leaves with an inhibition percentage of 54.56 % at 250 µg mL−1. Our finding showed that the essential oil of the flowers was the most active, with 64.623 % of inhibition against butyrylcholinesterase at 10 mg mL−1 from the incubation time of 30 min.
... The minimum inhibitory concentrations (MICs) were ascertained by the broth dilution method (microdilution using 96-well microplates). 31 The results presented in the Table showed that 9a is the most active towards Pseudomonas aeruginosa. We also noted that adding a CH 2 to the fragment R decreases this activity. ...
3-Substituted-1-phenyl-1 H -pyrazolo[3,4-d] pyrimidin-4-amines 2a-c were synthesized by treating 5-aminopyrazole-4-carbonitriles 1a-c with formamide. The reactivity of compounds 1a-c towards some cyclic anhydrides was studied. The condensation of 5-aminopyrazole-4-carbonitrile 1b with triethylorthoformate gives imidate 7b, which reacts with a series of primary amines and leads to pyrazolo[3,4-d]pyrimidine-4-amines 9 and 10. The reaction of imidate 7b with ammonia and hydroxylamine afforded pyrazolopyrimidine 2b and pyrazolo[3,4-d] pyrimidin-5-(4H)-ol 11, respectively. The synthesized compounds were completely characterized by H-1 NMR, C-13 NMR, IR, and HRMS. The antibacterial activity of some new synthesized compounds was evaluated and appeared to be significant.
... Antibacterial assay. MIC and MBC values were determined by a microtiter plate dilution method(Jabrane, Ben Jannet, Mastouri, Mighri, & Casanova, 2010) after dissolving the sample in 10% DMSO solution. Sterile 10% DMSO solution (100 lL) was pipetted into all wells of the micro-titer plate before transferring 100 lL of stock solution to the microplate. ...
... The essential oil of this species has been the subject of previous studies of chemical characterization, being possible the distinction of two types of oils: those largely dominated by monoterpene hydrocarbons, usually ␣-phellandrene, terpinolene, and p-cymene (Bicchi et al., 2009;Fleisher and Fleisher, 1996;Marongiu et al., 2007;Palá-Paúl et al., 2002, 2005; and those which also contain phenylpropanoids as major compounds or in appreciable amounts, usually myristicin and dillapiol (Jannet and Mighri, 2007;Jabrane et al., 2010). ...
Ridolfia segetum (L.) Moris essential oil was obtained by hydrodistillation and analysed by GC and GC-MS. The antioxidant properties were evaluated through the TBARS assay, and the in vitro anti-inflammatory activity was assessed through inhibition of NO production triggered by the Toll-like receptor 4 (TLR4) agonist, lipopolysaccharide (LPS), in mouse macrophages. Assessment of cell viability was made through a colorimetric assay using MTT on macrophages, keratinocytes, and hepatocytes.The main compounds are α-phellandrene (53.0-63.3%), terpinolene (11.9-8.6%), ß-phellandrene (5.5-6.0%), and dillapiol (1.9-8.0%). The oil demonstrated high antioxidant capacity in the concentrations tested (0.05-0.20. μL/mL) and significantly inhibited NO production without cytotoxicity in concentrations up to 1.25. μL/mL.The plants showed a high essential oil yield, which confers an industrial potential interest. Also, the high content of α-phellandrene (53.0-63.3%) makes it an important natural source of this compound.These results provide evidence of the therapeutic effects of this oil, and suggest that the anti-inflammatory activity in doses without cytotoxicity on mammalian cells, combined with its antioxidant potential and pleasant smell, could be of great value in the development of new phytopharmaceuticals.
... Due to its simplicity and sensitivity, some authors only use DPPH method for evaluating the antioxidant activities of essential oils. Recently, in our bibliographic research, some examples could be found [61][62][63][64][65][66][67][68][69][70][71][72][73][74]. Sometimes, the decision of only using this method can be attributed to the low antioxidant activity detected, therefore the authors consided it unnecessary to pursue other methods. ...
Essential oils are complex mixtures isolated from aromatic plants which may possess antioxidant and anti-inflammatory activities of interest in thye food and cosmetic industries as well as in the human health field. In this work, a review was done on the most recent publications concerning their antioxidant and anti-inflammatory activities. At the same time a survey of the methods generally used for the evaluation of antioxidant activity and some of the mechanisms involved in the anti-inflammatory activities of essential oils are also reported.
... The estimation of the MIC and minimal bactericidal concentration (MBC) was carried out by a microlitre plate dilution method (Celiktas et al. 2007;Jabrane et al. 2010). Dilutions of the essential oil were prepared to obtain concentrations ranging from 10 to 0.0775 mg/mL. ...
This study describes the chemical composition and evaluates the antibacterial and the cytotoxic effects of the essential oil from the flowers of Convolvulus althaeoides. Its chemical composition, determined by GC and GC-MS, is reported for the first time. A total of 24 compounds, accounting for 95.5% of the total oil, have been identified. The oil was characterised by a high proportion of sesquiterpene hydrocarbons (36.3%), followed by oxygenated sesquiterpenes (34.7%) and oxygenated monoterpenes (24.5%). The main compounds were germacrene D (12.5%), T-cadinol (11.8%) and verbenone (6.9%). The essential oil was tested for its antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Enterococcus faecalis and the clinical strain Acinetobacter sp. as well as facts cytotoxic activity towards the human breast cancer cells MCF-7. This oil did not exhibit significant antibacterial activity against the tested bacteria; however, it exerted a significant cytotoxic activity against the tested cell line (IC50 = 8.16 μg/mL).
Background
Natural products are secondary metabolites obtained from plants, animals, and microorganisms with diverse chemical structures resulting in diverse biological functions and drug-like properties.
Objective
This review article summarizes in detail the occurrence, detection, isolation, various pharmacological properties, metabolism, and toxicity of a natural compound i.e., 5-Allyl-1-methoxy- 2,3-methylenedioxybenzene commonly known as Myristicin.
Methods
A relevant literature search was made using the keywords essential oil, mace, myristicin, nutmeg, and pharmacological activities from different databases such as PubMed, Sci Finder, Science Direct, and Google Scholar. The literature search results presented articles from 1963 to 2022. Thereafter, the articles were carefully screened and selected for review.
Results
Myristicin, an alkoxy-substituted allylbenzene is present in major to minor amounts in the essential oils obtained from different plant parts and exhibits various pharmacological properties such as antimicrobial, antioxidant, antiproliferative, anti-inflammatory, insecticidal, and hepatoprotective. It forms 10 metabolites by reduction, demethylation, hydroxylation, ring formation, ring-opening, and conjugate formation. In the liver, myristicin has been metabolized by Cytochrome P450 complex enzymes to generate active metabolite (1ˈ hyroxymyristicin) responsible for cytotoxic, genotoxic and apoptotic effects (150 μM). But, myristicin at 600 μM does not produce enough 1ʼ-hydroxymyristicin to give the final toxicant.
Conclusion
Myristicin poses no major risk to human health through the consumption of herbs and spices due to its presence in low amounts. It has great potential to be used in the traditional system of medicine. We hope that this review will provide complete knowledge about myristicin on a single platform.
Medicinal chemists around the world have been inspired by nature and have successfully extracted chemicals from plants. Research on enzymatic modifications of naturally occurring compounds has played a critical role in the search for biologically active molecules to treat diseases.
This book set explores compounds of interest to researchers and clinicians. It presents a comprehensive analysis about the medicinal chemistry (drug design, structure-activity relationships, permeability data, cytotoxicity, appropriate statistical procedures, molecular modelling studies) of different compounds. Each chapter brings contributions from known scientists explaining experimental results which can be translated into clinical practice.
Volume 2 gives (1) a detailed overview of the sesquiterpenes polypharmacology, (2) an interesting journey around the world of cannabinoids that reveals the development of new synthetic Δ9-THC derivatives, (3) the design of specific formulations to overcome the volatility of small sized terpenes-based essential oils, (4) an update on the latest generations of endoperoxides endowed with antimalarial activity and finally (5) a summary of MedChem strategies to fix the most common issues in formulating terpene derivatives (like low potency and poor solubility).
The objective of this book set is to fulfill gaps in currently acquired knowledge with information from the recent years. It serves as a guide for academic and professional researchers and clinicians.
The IoT services composition is a complex task, where the necessary services choice and the handsets in the proper order as an integrated composite service is the main challenge in a highly constrained environment. The services composition has been the subject of research in several academic works where the authors try to find the best way to combine and compose the services in an optimal way. In this paper we examine the composition mechanism of IoT services, by focusing on QoS-aware approaches, by a comparative study of some proposed approaches in the literature.KeywordsServices compositionIoTInternet of ThingsQuality of serviceQoS
Current Security Information and Event Management (SIEM) systems use traditional information retrieval methods that produce heavy processing power, and then allocate their local resources to normalize collected logs for advanced correlation. Recently, a Mobile Agent-based SIEM was introduced that uses mobile agents for event collection and normalization at the source device in near real time. In this work, we introduce parallelization to MA-SIEM by comparing two approaches of normalization, the first approach is the multi-thread approach that is used by current SIEM systems, and the second one is the multi-agent approach that is used by MA-SIEM. Our results showed a promising performance gain if we combine both normalization approaches.KeywordsSIEMNormalizationMobile agentsMulti-threading
Senecio glaucus ssp. coronopifolius (Maire) and Ridolfia segetum (L.) are competitive-ruderal plants growing in Morocco. Their essential oils were tested for antifungal activity in vitro against Botrytis cinerea, agent of gray mold in plants, using volatile phase method (VF) and poisoned food method (PF). S. glaucus and R. segetum showed antifungal potential using VF method (68 and 80% inhibition at 640 μl/disc), and PF method (83 and 98% inhibition at 16 μl/ml), respectively. Accordingly, both essential oils are potential natural substitutes for chemical pesticides. Inhibition of fungal growth and simulations of synergistic interactions are facilitated by use of plant oils. Qualification of essential oils using preliminary fuzzy models specifies the groups of units, which create formulation design and prediction of inhibition. The latter can be expanded in simulations of synergy in variable scenarios.KeywordsSynergySimulationFormulationEssential oilsFuzzy models
A series of ursolic acid (UA), oleanolic acid (OA) and 18β-glycyrrhetinic acid (GA) derivatives were synthesized by introducing a range of substituted aromatic side-chains at the C-2 position after the hydroxyl group at C-3 position was oxidized. Their antibacterial activities were evaluated in vitro against a panel of four Staphylococcus strains. The results revealed that the introduction of aromatic side-chains at the C-2 position of GA led to the discovery of potent triterpenoid derivatives for inhibition of both drug sensitive and resistant S. aureus, while the other two series derivatives of UA and OA showed no significant antibacterial activity even at high concentrations. In particular, GA derivative 33 showed good potency against all four strains of Staphylococcus (MIC = 1.25 - 5 μmol/L) with acceptable pharmacokinetics properties and low cytotoxicity in vitro. Molecular docking was also performed using S. aureus DNA gyrase structure to rationalize the observed antibacterial activity. Therefore, this series of GA derivatives have strong potential for the development of a new type of triterpenoid antibacterial agent.
The Talassemtane National Park (PNTLS) represents a significant biome for flora diversity in Morocco and North Africa. Based on its floristic richness and on the rural lifestyle of its population, we hypothesize that the inhabitants of the park hold a substantial knowledge of medicinal plants. The Apiaceae is one of the 20
largest plant families, and one with the significant higher proportion of medicinal plants. The aim of this study is to deepen the knowledge on the traditional medicinal uses in Morocco within this family. A three year survey (2014�2017) was conducted following ethnobotanical field-research methods. We identified 31 taxa (species and subspecies) belonging to 16 genera. With a total of 1430 use reports, we have identified 72 medicinal uses to treat 48 conditions or symptoms classified into 15 pathological groups according to the
international classification of primary care (ICPC). Highlighted ones are D-digestive system (32% of uses), A-general (12%), S-cutaneous (11%) and U-urological (8%). The most common mode of administration is oral (78%) and the majority of remedies are prepared as a decoction (55%). Original data were found on the medicinal
use of several species of genus Eryngium, Stoibrax, Elaeoselinum, Torilis and Apium, which were not previously reported in other territories in Morocco.
The main objective of this paper is to discuss the viable resilience of supply chains. Resilience, durability and performance in the supply chain have to remain unchanged at acceptable levels in the presence of potential disruption. Thus, supporting performance while minimizing the spread and severity of risks through practical capacities for regulated but balanced resilience and sustainability is the biggest supply chain challenge. We seek, through the seventeen hypotheses, built based on the relevant theoretical frameworks (normal accident theory; systemic risk theory; resource dependence theory and high reliability of organization theory), to justify the meaning of complementarity between the concepts of vulnerability, resilience and sustainability of supply chain.
A new series of antibacterial pyrazolo-triazolo-pyrimidine derivatives 3a-3i were synthesized in two steps starting from aminopyrazole 1 and characterized by ¹H NMR ¹³C NMR and HRES-MS. Their molecular geometry are also calculated by the Density Functional Theory (DFT) employing B3LYP level with 6-311G (d,p) basis set. All the synthesized compounds were tested for in vitro antibacterial activity against a panel of selected bacterial strains, by application of the Disc-Diffusion and MIC assays, using gentamicin as standard. The interactions of these compounds with the bacteria Pseudomonas aeruginosa (LasR) were performed by molecular docking studies.
Urban waste collection is a highly visible municipal service which consists of large expenditures and difficult operational issues. In addition, it is very costly to operate in terms of investment costs (i.e. vehicles fleet), operational costs (i.e. fuel and maintenances) so that generating small improvements in this field can lead to large savings in municipal expenditures. Among these problems raised in the process of decisions making by managers and associated policymakers, one can respect the determination of the optimal weekly policies of waste collection. In this paper, a periodic capacitated arc routing problem (PCARP) is described by designing a smart model of considering mobile disposal sites. The aim is to minimize total cost and present a financial planning for related organizations such as municipalities. In other words, the aim is to determine the optimal routes for all of the required edges (streets or alleys with positive demands) per week, number and locations of the mobile disposal sites, and the number of the used vehicles. In order to solve the problem, two optimization algorithms based on simulated annealing (SA) are proposed, which have different cooling schedules. Then, CPLEX solver is used in order to evaluate the performance of these algorithms in small-sized problems. The experimental results show that the algorithms have appropriate performance in a reasonable computational time.
Background
Fusidic acid (FA) (WU-FA-00) is the only commercially available antimicrobial from the fusidane family that has a narrow spectrum of activity against Gram-positive bacteria.
Methods
Herein, the hydrogenation derivative (WU-FA-01) of FA was prepared and both compounds were examined against a panel of six bacterial strains. In addition, their anti-inflammatory properties were evaluated using a 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced mouse ear edema model.
Results
The results of the antimicrobial assay revealed that both WU-FA-00 and WU-FA-01 displayed a high level of antimicrobial activity against Gram-positive strains. Moreover, killing kinetic studies were performed and the results were in accordance with the minimum inhibitory concentration and minimum bactericidal concentration results. We also demonstrated that the topical application of WU-FA-00 and WU-FA-01 effectively decreased TPA-induced ear edema in a dose-dependent manner. This inhibitory effect was associated with the inhibition of TPA-induced upregulation of proinflammatory cytokines IL-1β, TNF-α, and COX-2. WU-FA-01 significantly suppressed the expression levels of p65, IκB-α, and p-IκB-α in the TPA-induced mouse ear model.
Conclusion
Overall, our results showed that WU-FA-00 and WU-FA-01 not only had effective antimicrobial activities in vitro, especially to the Gram-positive bacteria, but also possessed strong anti-inflammatory effects in vivo. These results provide a scientific basis for developing FA derivatives as antimicrobial and anti-inflammatory agents.
The synthesis and pharmacological evaluation of new series of 4-((3-aryl-4,5-dihydroisoxazol-5-yl)methoxy)-2H-chromen-2-ones 3a–f prepared by cycloaddition reaction using various arylnitrile oxides with the suitable 4-(allyloxy)-2H-chromen-2-one 2a are described. The 2-methyl-2,3-dihydrothieno[3,2-c]chromen-4-one 8 was also synthesized due to chemospecificity by the thio-Claisen rearrangement of 4-(allylthio)-2H-chromene-2-thione 7a. We also describe the new heterocyclic compounds 4-(R-thio)-2H-chromene-2-thiones 7a–d, 4-(2-thioxo-2H-chromen-4-ylthio) 5 and 4,4′-thiobis (2H-chromen-2-one) 6 which were prepared by a classical and PTC alkylation of 4-mercapto-2H-chromene-2-thione 4 with allylic halides.
The antimicrobial activity of essential oils is discussed in this review taking in account studies which were published in the period of time from 2008 until September 2010. Furthermore, the most important methods to examine the antimicrobial efficiency of essential oils are presented. The studies are divided into the following two groups, namely antibacterial and antifungal active agents depending on the activity of the applied essential oil against the test microorganisms. Various interesting possible applications are revealed such as the use of essential oils instead of synthetic drugs to circumvent the increasing resistance of some pathogens. Moreover, they could not only be used for the therapy of infectious illnesses, but also as preservatives in the food industry. A further possibility is, among others, the application of essential oils in skin products in order to treat or avoid dermal infections. Additionally, the prevalent constituents of the individual antimicrobial active essential oils are elaborated. Copyright © 2011 John Wiley & Sons, Ltd.
The present study describes the chemical composition, antibacterial and antifungal activities of essential oils from Bidens pilosa, a traditional medicinal plant widely distributed in the subtropics and tropics. The essential oils from the fresh leaves and flowers of B. pilosa were analyzed by GC–MS. Forty-four components were identified, of which β-caryophyllene (10.9% and 5.1%) and τ-cadinene (7.82% and 6.13%) were the main compounds in leaves and flowers, respectively. The oils and aqueous extracts of leaves and flowers were subjected to screening for their possible antioxidant activities by using 2,2′-diphenyl-1-picrylhydrazyl (DPPH) and β-carotene bleaching methods. In the former case, the essential oils from leaves and flowers were found to be superior to all aqueous extracts tested with an IC50 value of 47.5 and 49.7μg/ml, respectively, whereas all extracts and essential oils seemed to inhibit the oxidation of linoleic acid in the latter case. The oils from B. pilosa exerted significant antibacterial and antifungal activities against six bacteria and three fungal strains. The inhibitory activity of the flower essential oils in Gram-negative bacteria was significantly higher than in Gram-positive. Our findings demonstrate that the essential oils and aqueous extracts of B. pilosa possess antioxidant and antimicrobial activities that might be a natural potential source of preservative used in food and other allied industries.
The present study was conducted to evaluate the antimicrobial activities, antioxidant and properties of essential oils and methanol extracts of Origanum vulgare ssp. vulgare plants. The chemical composition of a hydrodistilled essential oil of O. vulgare ssp. vulgare was analyzed by a GC/MS system. A total 62 constituents were identified. Caryophyllene and spathulenol were found to be the main constituents, followed by germacrene-D and α-terpineol. Antioxidant activity was measured employing two methods namely, scavenging of free radical DPPH and the inhibition of linoleic acid oxidation by methanol extracts and the essential oil of O. vulgare ssp. vulgare. Antioxidant studies suggested that methanol extract behaved as a strong free radical scavenger providing IC50 at only 9.9 μg/ml, whereas the oil showed weaker activity with IC50 at 8.9 mg/ml. Total phenolic constituents based on gallic acid equivalents revealed the presence of total soluble phenolics in the extract as 220 μg/mg dry extract (22%, w/w) and, most probably, they are responsible for the radical scavenging activity of methanol extracts. Methanol extract was not effectively able to inhibit linoleic acid oxidation and only 32% inhibition was achieved at 2 mg/ml concentration, far below that of the positive control (butylated hyroxytoluene, BHT) at the same concentration. However, 2.2 mg/ml essential oil solutions provided 50% inhibition in the linoleic acid oxidation test system.
Agar diffusion techniques are used widely to assay plant extracts for antimicrobial activity, but there are problems associated with this technique. A micro-dilution technique was developed using 96-well microplates and tetrazolium salts to indicate bacterial growth. p-Iodonitrotetrazolium violet [0.2 mg/ml] gave better results than tetrazolium red or thiazolyl blue. The method is quick, worked well with Staphylococcus aureus, Enterococcus faecalis, Pseudomonas aeruginosa, and Escherichia coli and with non-aqueous extracts from many different plants. The method gave reproducible results; required only 10-25 microliters of extract to determine minimal inhibitory concentrations, distinguished between microcidal and microstatic effects, and provided a permanent record of the results. Using S. aureus, and a Combretum molle extract, the technique was 32 times more sensitive than agar diffusion techniques and was not sensitive to culture age of the test organism up to 24 hours. The S. aureus culture could be stored up to 10 days in a cold room with little effect on the assay results. This method was useful in screening plants for antimicrobial activity and for the bioassay-guided isolation of antimicrobial compounds from plants. MIC values determined for sulfisoxazole, norfloxacin, gentamicin, and nitrofuratoin were similar to values indicated in the literature but values obtained with trimethroprim and ampicillin were higher with some bacteria.
The essential oil and methanol extracts from A. biebersteinii Afan. (Asteraceae) were evaluated for their antimicrobial and antioxidant activities in vitro. The oil showed stronger antimicrobial activity than the extracts. Their antioxidant features were also evaluated using diphenyl-1-picrylhydrazyl (DPPH), inhibition of superoxide and hydroxyl radicals and inhibition of the lipid peroxidation assays. Particularly, polar subfraction of the methanol extract showed antioxidant activity. The GC-MS analysis of the oil has resulted in the identification of 23 components; piperitone, eucalyptol, camphor, chrysanthenone and borneol were the main components. Antimicrobial activity tests carried out with the fractions of the oil showed that the activity was mainly observed in those containing eucalyptol and camphor, in particular, followed by borneol and piperitone.
Seasonal variation in chemical composition of essential oils obtained from Satureja parnassica subsp. parnassica Heldr. & Sart ex Boiss. and Satureja thymbra L. was determined by GC and GC-MS analysis. The in vitro antibacterial activities of these essential oils were evaluated at two different initial levels against two common foodborne bacteria. Their minimum inhibitory concentration (MIC) and noninhibitory concentration (NIC) values were determined via an innovative automated technique, which was applied on a Malthus apparatus combining the conductance measurements with the common dilution method. The essential oil concentration fluctuated greatly during the period examined and established that the Satureja oils obtained during the flowering period were the most potent, exhibiting the lowest MIC values and retaining remarkable bactericidal properties. Thus, they represent an inexpensive source of natural antibacterial substances that exhibit potential for use in food systems to prevent the growth of foodborne bacteria and to extend the shelf life of the processed food.
The essential oil of black cumin seeds, Nigella sativa L., was tested for a possible antioxidant activity. A rapid evaluation for antioxidants, using two TLC screening methods, showed that thymoquinone and the components carvacrol, t-anethole and 4-terpineol demonstrated respectable radical scavenging property. These four constituents and the essential oil possessed variable antioxidant activity when tested in the diphenylpicrylhydracyl assay for non-specific hydrogen atom or electron donating activity. They were also effective ·OH radical scavenging agents in the assay for non-enzymatic lipid peroxidation in liposomes and the deoxyribose degradation assay.
The analysis of natural mixtures is commonly carried out by GC(RI), GC-MS, GC-IRFT, HPLC-MS or a combination of these techniques. In a different approach, 13C NMR spectroscopy could be used for the non separative identification of the individual components of complex mixtures (essential oils, resins, extracts, vegetable oils, ...). Following the pioneering work of Formácek and Kubeczka, we developed an experimental procedure, based on the computer-aided analysis of the 13C-NMR spectrum of the mixture, which allows the identification of the main components of essential oils and extracts. We analysed a large number of essential oils containing components bearing diverse skeletons and functions. This method allowed an accurate identification of terpenes (including stereoisomers, diastereoisomers and other compounds which exhibit insufficiently resolved mass spectral patterns or which co-eluate on GC as well as thermolabile compounds) in essential oils and solvent extracts. In this review we will report on the utilisation of C-NMR for the unambiguous identification of unusual terpenes present in essential oils from Labiatae, its efficiency and its complementarity with conventional techniques. The complete analysis, by GC(RI), GC-MS and 13C-NMR spectroscopy, of some complex essential oils is reported. Examples are chosen among the following species: Calamintha nepeta, Clinopodium ascendens, Lavandula dentata, L. stoechas, Rosmarinus officinalis, Salvia guaranitica, Stachys glutinosa, Teucrium polium ssp capitatum, Thymus herba barona, T. carnosus, T. camphoratus, T. caespititius.
The flower oil of Ridolfia segetum (L.) Moris of Tunisian origin was analyzed by GC and GC/MS. The main constituents of the oil were myristicin and dillapiole, the amounts of which varied depending upon the length of time the flowers were hydrodistilled. The contents of myristicin and dillapiole varied from 13.1–31.5% and 29.5–85.4%, respectively. Oil samples (fractions) were taken every 10 min from 10 to 150 min. Each fraction was screened against three Gram-positive and three Gram-negative bacteria. It was found that the antibacterial activity of the fractions was directly related to their proportions of monoterpenols and phenolic derivatives.
The oils isolated from the aerial parts of Ridolfia segetum (L.) Moris (Apiaceae) gathered in Castilla la Mancha (Spain) were analyzed by capillary GC and GC/MS. The oil from the flowers was dominated by α-phellandrene (32.0–33.8%), terpinolene (18.0–21.4%) and (Z)-β-ocimene (12.4–14.5%), while the main components of the fruit oils were found to be dillapiole (5.1–39.6%), β-pinene (10.3–20.9%), α-pinene (3.0–16.1%), α-phellandrene (13.7–15.3%) and (Z)-β-ocimene (8.1–12.8%). The oil from the stems was characterized by a high content of p-cymene (15.1–79.5%), (Z)-β-ocimene(0.9–38.5%) and α-phellandrene (1.1–14.4%), whereas the oil from the leaves was shown to contain p-cymene (8.8–83.6%), (Z)-β-ocimene (t-32.6%), myrcene (t-12.5%) and β-pinene (2.1–12.1%) as major constituents.
The volatile oils of the different aerial parts of Ridolfia segetum (L.) Moris (Apiaceae) gathered in Andalucia (Spain) were analyzed by capillary GC and GC/MS. The oil from the stems was characterized by a high content of α-phellandrene (39.4–62.0%), p-cymene (10.4–22.7%), (Z)-β-ocimene (10.2–11.7%) and terpinolene (7.0–15.6%), whereas the leaf oil was shown to contain α-phellandrene (61.8%-69.5%), (Z)-β-ocimene (10.7–12.0%) and terpinolene (6.0–10.7%) as major constituents. The flower oil was also dominated by α-phellandrene (44.5–54.7%), (Z)-β-ocimene (8.5–10.6%) and terpinolene (20.1–27.6%), while the main components of the fruit oils were found to be β-pinene (1.5–11.9%), α-phellandrene (5.2–56.9%), p-cymene (4.2–25.2%), β-phellandrene (0.9–15.6%), terpinolene (4.3–12.5%) and dillapiole (0.1–45.7%).
The volatiles obtained separately from the leaves and flowers of Ridolfia segetum (L.) Moris collected from three locations in Israel were studied by capillary GC/MS. The main components in the flower volatile concentrate were α-phellandrene (44.1–48.9%), piperitenone oxide (8.3–18.0%) and terpinolene (11.8%-16.3%) while α-phellandrene (29.8–37.1%), piperitenone oxide (8.2–14.2%) and p-cymene (8.4–15.2%) were the main components of the leaf volatile concentrate. In general, the flowers possessed a richer composition. Such constituents as elemicin, myristicin and nepetalactone were found only in the flowers. The most outstanding feature of the flower volatiles was the presence of dill apiole (about 3%) which was not detected in the leaves.
We report a methodology that allows identification and quantitative determination of individual acidic and neutral diterpenes in natural mixtures, using the computer-aided analysis of their 13C-NMR spectra. The analytical procedure was validated on artificial mixtures and then applied to authentic oleoresins of Pinus nigra. Up to eleven diterpenes, which represented 63% of the total composition of the oleoresin, were identified and quantified without previous separation or derivatization.
Four new iridoid glucosides 1–4, named blumeosides A–D, were isolated from the methanolic stem-bark extract of Fagraea blumei G. DON. (Loganiaceae). They were accompanied by the benzyl-alcohol derivative di-O-methylcrenatin (5) and the flavone C-glucoside swertisin (6). The structures of 1–4 were established by spectroscopic methods, including FAB-MS, and 1H- and 13C-NMR, and by alkaline hydrolysis. Blumeosides A (1) and C (3) are 10-O-(2,5-dihydroxytercphthalo) adoxosidic acid and 10-O-(2-hydroxyterephthalo)adoxosidic acid, respectively. In blumeosides B (4) and D (2), both carboxylic groups of the terephthalic-acid moiety are esterified by adoxosidic-acid units, Blumeosides A–D (1–4) inhibited bleaching of crocin induced by alkoxyl radicals. Blumeosides A (1) and D (2) also demonstrated scavenging properties towards the 2,2-diphenyl-1-picryl-hvdrazvl (CDPPH) radical in TLC autographic and spectrophotometric assays.
Rosmarinus officinalis is widely found in the lands of Aegean and Mediterranean regions of Turkey. The goal of this work was to test the antimicrobial activity of the essential oils and methanolic extracts of R. officinalis collected from three different regions at four different time intervals of the year against Staphylococcus aureus, Proteus vulgaris, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterococcus feacalis, Escherichia coli, Staphylococcus epidermidis, Bacillus subtilis and Candida albicans. Essential oils were obtained from the aerial parts of the plant by using a Clevenger apparatus, for 4 h. After distillation, the distillates were filtered, air-dried and then extracted by using a Soxhlet apparatus for 9 h to obtain the methanolic extracts. The antimicrobial activities of the methanolic extracts were tested by the disc diffusion technique. The antimicrobial activities of the essential oils obtained from R. officinalis were determined by minimum inhibitory concentration (MIC).The results indicated that the tested bacteria were sensitive to the essential oils and partially to the methanolic extracts. The antimicrobial activities of the essential oils against the tested bacteria differed, depending on location and seasonal variations.
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.
The present study was conducted to evaluate in vitro antibacterial and antioxidant properties of essential oil and methanol extracts from a unique and endemic plant, Zataria multiflora Boiss. The antibacterial test results showed that the essential oil of the plant strongly inhibited the growth of all of the microorganisms studied especially the Gram-negative strains. The polar fraction of methanol extract has been effective against Gram-positive strains, while the non-polar fraction has shown activity similar to essential oil. The antioxidant potential of the samples was evaluated using two separate methods, inhibition of free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ammonium thiocyanate systems. Sub fractions of the methanol extract were able to reduce the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH) with an IC50 of 11.7 ± 1.58 and 16.2 ± 1.61 μg/ml, respectively for non-polar and polar ones, which the activity of the latter almost is equal to synthetic antioxidant BHA (18.2 ± 1.94 μg/ml). Inhibition values of linoleic oxidation were calculated to be 82.4% and 80.3% for the polar and non-polar fractions, respectively. The essential oil to be showed more inhibition (89.7 ± 2.5), similar to the synthetic antioxidants BHA (97.8 ± 2.94) and ascorbic acid (93.2 ± 2.1). The chemical composition of hydrodistilled essential oils of Z. multiflora was analyzed by GC/MS. A total of 25 compounds representing 99.78% of the oil were identified: thymol (37.59%), carvacrol (33.65%); para-cymene (7.72%), γ-terpinene (3.88%) and β-caryophyllene (2.06%) were the main components comprising 84.9% of the oil. Results here show that the essential oil and methanol extract of Z. multiflora possess antioxidant and antibacterial activity, and therefore it could be used as a natural preservative ingredient in food and/or pharmaceutical industries.
The total phenolic content and related total antioxidant capacity of 70 medicinal plant infusions was analyzed. Infusions were prepared in common way in which teas are prepared for human consumption. The total phenolics were measured by Folin–Ciocalteau assay. The total antioxidant capacity was estimated by Ferric Reducing/Antioxidant Power (FRAP) assay. To make practical comparison of relative antioxidant potential of phenolics extracted from selected medicinal plants, the phenol antioxidant coefficient (PAC) was calculated for each infusion. The total phenolic content of medicinal plant infusions ranges from 9 to 2218 mg/L. The FRAP range from 0.06 to 25 mM/L. There was significant linear correlation between total phenolic content and FRAP. According to their antioxidant capacity, 70 medicinal plant extracts can be divided in five groups: (a) very low FRAP (<1 mM/L) n = 9; (b) low FRAP (1–5 mM/L), n = 37; (c) good FRAP (5–10 mM/L), n = 15; (d) high FRAP (10–20 mM/L), n = 8; and (e) very high FRAP (>20 mM/L), n = 1 medicinal plant extract. The PAC was ranging from 1.1 to 3.9 (average 2.4). The best results were obtained for Melissae folium infusions: high phenolic concentration, very high FRAP (>20 mM/L) and PAC > 3. The effect of infusion time and infusion temperature on the phenolic content, FRAP, and free radical scavenging ability was tested. DPPH radical scavenging ability of Melissae folium phenolics was similar to (+)-catechin but not as good as for quercetin. Compared to Trolox and vitamin C, Melissae folium phenolics were more efficient free ABTS radical scavengers. The results indicate that Melissae folium infusions could be an important dietary source of phenolic compounds with high antioxidant capacity comparable with red wine or beverages like tea.
The present paper examines the chemical composition and antioxidant capacity of free volatile aglycones from basil compared to their essential oil. The comparison of chemical composition of volatile aglycones with the chemical composition of essential oil reveals four common compounds: eugenol, chavicol, linalool and α-terpineol. For the evaluation of the mentioned antioxidant capacities, two different methods were performed: the 2,2′-diphenyl-1-picrylhydrazyl radical scavenging method (DPPH) and ferric reducing/antioxidant power assay (FRAP). DPPH method shows that free volatile aglycones possess good antioxidant properties comparable with that of the essential oil and well-known antioxidant butylated hydroxytoluene (BHT), but less than pure eugenol. The results obtained by FRAP method show that these compounds are some less effective antioxidants than essential oil and BHT.
A total of 76 extracts from 35 plants available in the Turkish flora were assayed for their in vitro antibacterial activities against five pathogenic bacteria and a yeast. Sixteen crude extracts from eight plant species were found to possess an activity against at least one or more test microorganisms. Bioassay-guided fractionation of the most active crude extracts was also carried out with the most active extracts. Activity against Staphylococcus aureus, Bacillus cereus, Branhamella catarrhalis, Escherichia coli, Clostridium perfringens and Candida albicans (yeast) is discussed.
The essential oil of black cumin seeds, Nigella sativa L., was tested for a possible antioxidant activity. A rapid evaluation for antioxidants, using two TLC screening methods, showed that thymoquinone and the components carvacrol, t-anethole and 4-terpineol demonstrated respectable radical scavenging property. These four constituents and the essential oil possessed variable antioxidant activity when tested in the diphenylpicrylhydracyl assay for non-specific hydrogen atom or electron donating activity. They were also effective.OH radical scavenging agents in the assay for non-enzymatic lipid peroxidation in liposomes and the deoxyribose degradation assay. GC-MS analysis of the essential oil obtained from six different samples of Nigella sativa seeds and from a commercial fixed oil showed that the qualitative composition of the volatile compounds was almost identical. Differences were mainly restricted to the quantitative composition.
GC-MS analysis of essential oils of Iranian Mentha piperita and Myrtus communis extracted by hydrodistillation lead to identification of 26 and 32 compounds, respectively. The oils had good to excellent antimicrobial activities against Escherichia coli, Staphylococcus aureus and Candida albicans with the oil of M. piperita being more active. The findings suggest feasibility of application of M. piperita oil in treatment of the infections caused by C. albicans and E. coli. D-values on exposure to M. piperita and Myrtus communis oils were (2.14 and 2.8min), (1.4 and 12.8min) and (4.3 and 8.6min) for E. coli, S. aureus and C. albicans , respectively. The oils were screened for their possible antioxidant activities by two complementary test systems, namely DPPH free radical scavenging and beta-carotene/linoleic acid systems. M. piperirta oil exerted greater antioxidant activity than that of M. communis. Phytochemical and phytobiological characteristics of these oils may lead to extraction and production of active compounds in single or combined forms with useful applications.
Supercritical carbon dioxide extraction allowed to obtain the volatile oil of different aerial parts of Ridolfia segetum (L.) Moris. Extraction conditions were as follows: pressure, 90 bar; temperature, 50 degrees C and carbon dioxide flow, Phi = 1.0 kg h(-1). Waxes were entrapped in the first separator set at 90 bar and -10 degrees C. The oil was recovered in the second separator working at 15 bar and 10 degrees C. The main components of the flower oil were alpha-phellandrene (19.4%), terpinolene (20.5%), piperitenone oxide (11.6%), beta-phellandrene (8.2%), (Z)-beta-ocimene (7.8%), myristicin (7.5%) and p-cymene (4.4%). The comparison with the hydrodistilled (HD) oil reveal that the significative difference was the content of sesquiterpenes which are higher in the supercritical fluid extraction (SFE) products. Collection of samples at different extraction times during supercritical extraction, allowed to monitor the change of the oil composition. Lighter compounds, as hydrocarbon monoterpenes, were extracted in shorter times than the heavier hydrocarbon and oxygenated sesquiterpenes. The oil from the steams was characterized by a high content of alpha-phellandrene (12.9%), terpinolene (11.6%), myristicin (11.0%), p-cymene (9.9%), beta-phellandrene (8.2%) and (Z)-beta-ocimene (6.0%) while the main components of the fruits were found to be myristicin (70.8%), piperitenone oxide (19.9%) and dill apiole (4.2%).
Essential oil of Ridolfia segetum
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13 C NMR as a tool for identification of individual components of essential oils from Labiatae
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