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Enantiomer-specific identification of chiral molecules in natural extracts is a challenging task, as many routine analytical techniques fail to provide selectivity in multicomponent mixtures. Here we describe an alternative approach, based on the combination of ion mobility–mass spectrometry (IM-MS) and quantum chemistry (QM), for the direct enantiomers differentiation in crude essential oils. The identification of a-bisabolol enantiomers contained in the raw essential oil (EO) from the Corsican Xanthium italicumfruits is reported as a proof-of-concept. Accordingly, IM-MS experiments performed in Ag+-doped methanol revealed the presence of both (+)- and (-)-a-bisabolol in the EO, while molecular simulations provided the structures of the two a-bisabolol enantiomer silver(I) adducts.

AbstractAngiogenes is therefore appears to be a complex phenomenon, finely regulated by various activators (pro-angiogenic factors) and inhibitors (anti-angiogenic factors). Among the pro-angiogenic factors, VEGF (Vascular Endothelial Growth Factor) seems to be one of the main players in tumor angiogenesis. It exerts its pro-angiogenic activity by attaching to the surface of receptors with tyrosine kinase activity (VEGFR). The aim of this research was the bioinformatical study of VEGFR inhibition by essential oils of the Inula viscosa.Analyses of essential oils obtained by hydrodistillation from the aerial parts of the plant were performed using GC and GC/MS analysis. We used molecular modeling approaches as molecular mechanics to theoretical investigation VEGF receptors by natural inhibitors.Nineteen compounds were identified, constituting 90.1-98.8% of the total essential oils. The main components of the plants were (E)-nerolidol (15.5–20.2 %), caryophyllene oxide (10.6–18.1%), (E)-Z-farnesyl acetone (13.2–25.1%) and (E)-β-farnesene (1.5–5.6%). Essential oil samples were clustered into two groups according to their chemical compositions. The molecular dynamics study was conducted for the best inhibitors. A few key residues were identified at the binding site of VEGFR. The Pharmacokinetics was justified by means of lipophilicity and high coefficient of skin permeability. The in silicoevaluation of ADME revealed that L19 has high absorption. The essential oil of I. viscosapresents a significant variability. This study revealed that (E)-Z-Farnesylacetone is a functional inhibitor of VEGF activities and subsequently can be the best inhibitors candidate to be scrutinized in vivoand in vitro.Communicated by Ramaswamy H. Sarma

AbstractMany pro-angiogenic factors acting directly or indirectly on the proliferation and differentiation of endothelial cells have been highlighted, in particular: VEGF (‘Vascular Endothelial Growth Factor’), FGF (‘Fibroblast Growth Factor’), PDGF (‘Platelet-Derived Growth Factor’), VEGF exerts its pro-angiogenic activity by binding to the surface of receptors with tyrosine kinase activity (VEGFR). The first objective of this study was to elucidate the composition of the essential oil of the roots of Scolymus grandiflorasDesf. The second aim was to describe the intra-species variation in essential oil composition in natural populations of 21 oil samples from different Algerian locations using statistical analysis and bioinformatical study of VEGFR inhibition. The essential oil isolated from the root parts, was a really source of Davanoide compounds. The results of the docking simulation revealed that davanone (Ligand 13) has an affinity to interact with cDNA, VEGF and its receptors. The ADMET properties and BOILED-Egg plot validate the compound 13 pass the brain barrier and have high absorption in the intestines with good bioavailability. The findings of this study contribute to the pharmacological knowledge and the therapeutic efficacy of davanone and can initiate the development of new anti-angiogenic drugs. Results showed that essential oil of Scolymus grandifloruspresented a large level of percentage of davanone, davanol D1 and 2-hydroxy davanone. These components may be a new source of nontoxic anticancer agents. However, an additional in vitroand/or in vivoexperimental study should make it possible to verify the theoretical results obtained in silico.Communicated by Ramaswamy H. Sarma

AbstractIn recent years, growing attention has been given to essential oils. Essential oils obtained from medicinal plants show high therapeutic potential against various types of pathologies, including Alzheimer's, cancer and inflammatory diseases. The purpose of this work was to study the chemical composition of the aerial and root parts of Centaurea acaulisessential oils by GC/FID and GC/MS, to evaluate the anti-inflammatory, antioxidant and neuroprotective properties, and in-vitrocombinatory effect of aplotaxene isolated from the roots with reference standards, in order to find new and more effective agents for the treatment of degenerative and inflammatory diseases. The statistical analysis clustered the essential oil aerial parts into two distinct groups. The specimens characterized by a humid climate and low altitude was mainly discriminated by the high contents of (E)-β-caryophyllene (3.4-8.4%), hexadecanoic acid (6.3-10.8%) and caryophyllene oxide (6.2-9.9%). While the second group characterized by a humid climate and higher altitudes was characterized by high levels of limonene (15.2-19.2%) and τ-muurolol (12.6-17.2%). In contrast, essential oils of roots were dominated by aplotaxene whatever the climate type. All samples showed very good antioxidant and anti-inflammatory activities. The combination of aplotaxene with references gave synergistic effects with excellent activities about 2 times higher than the synthetic references. The neuroprotective activity of essential oils and aplotaxene did not show inhibition against AChE, whereas they inhibited BChE with IC50values comparable to Galantamine.

AbstractThe purpose of this work was to study the chemical composition and in vitroantioxidant, antimicrobial and anti-inflammatory activities of essential oil and carlina oxide isolated to Carlina hispanicaroots. The in vitrocombinatory effect of carlina oxide with BHT, EDTA and diclofenac to reduce their minimum effective dose and minimize their side effects was also tested. The essential oil obtained from the roots has been studied using GC and GC/MS. Antioxidant activity was assessed using radical scavenging activity (DPPH), the β-carotene bleaching test using the BHT as a positive control, and the ferrous Iron chelating using EDTA as a positive control. The activity of anti-inflammatory was assessed by the protein denaturation method using the diclofenac as a positive control. The antimicrobial activity was evaluated against six microbial strains using the Disc Diffusion Assay and the microplate method to determine the MIC. The essential oil of C. hispanicawas represented mainly by an acetylenic compound carlina oxide (81.1 %) which was isolated and identified by spectroscopic 1H NMR, 13C NMR and IR methods. The results of the biological activities showed that both essential oil and carlina oxide had an interesting antioxidant and anti-inflammatory power. Likewise, the combinations of positive controls with carlina oxide showed better activities with a substantial reduction in inhibitory concentrations and dose of the antioxidants and anti-inflammatories synthetics. Further studies are needed to provide these positive control combinations with carlina oxide in the pharmaceutical industry. Keyworlds: Carlina hispanica, essential oil, carlina oxide, biological activities.

Background: Infectious diseases are responsible for millions of deaths a year worldwide. Antibiotics, which have saved so many lives and improved life expectancy, may become ineffective due to a worrying increase in bacterial resistance. Some of the appropriate actions that could be initiated to address this problem are to develop and search for new antimicrobial substances from medicinal plants, and combine antibiotics with antimicrobials agents isolated from a reservoir of bioactive natural products. Objectives: The purpose of this work was to study the chemical composition of the essential oil and hydrosol extract of Plumbago europaea, to evaluate their in-vitro antimicrobial activities and evaluate in-vitro combinatory antimicrobial effect of hydrosol extract with Gentamicin and Amphotericin B against a large panel of microorganisms in an effort to reduce their minimum effective dose and minimizing their side effects. Methods: The essential oil and hydrosol extract obtained from the roots of Plumbago europaea were analyzed by GC/MS and tested for their antibacterial and antifungal activities against twelve different strains of microorganisms. The effectiveness, in-vitro, of the association between the hydrosol extract and both Gentamicin and Amphotericin B was also investigated using the checkerboard method. Results: The obtained results revealed that nine and four components, representing for 92.4% and 97.4% of the total essential oil and hydrosol extract composition were identified, respectively and hydrosol extract was more active than the essential oil against all screened microorganisms, with interesting MIC values (19 μg/mL). An important effect of hydrosol extract was obtained in decreasing the MIC of Gentamicin and Amphotericin B in all tested combinations. Conclusion: The in-vitro combination of the hydrosol extract with Gentamicin and Amphotericin B led to substantial MIC reduction against all tested microorganisms. This combination can help to reduce the minimum effective dose of antimicrobial drugs used, which may help to decrease their side effects; and deliver these medicines with similar potency.

ABSTRACTChemical composition of the essential oils of three subspecies of Algerian Thymus munbyanus Boiss. & Reut. (subsp. abylaeus, subsp. ciliatus and subsp. coloratus)aerial parts have been investigated. GC and GC/MS analysis allowed the identification of sixty-eight compounds accounting for 99.3%, 99.7% and 98.2% of collective essential oils of three subspecies. The main components of three collective essential oils were: α-terpinyl acetate (51.7%), α-terpineol (9.7%), borneol (6.8%) and bornyl acetate (5.2%) for subsp. abylaeus; carvacrol (65.7%), γ-terpinene (13.6%) and p-cymene (7.9%) for subsp. ciliatus and camphor (25.9%), myrcene (16.9%), 1,8-cineole (6.5%) and camphene (6.2%) for subsp. coloratus. Intra-species variations of chemical compositions of essential oil from thirty-five Algerian samples were also investigated using statistical analysis. Essential oils samples were discriminated in three main clusters confirming relation between the chemical compositions and taxonomical differentiation between the three subspecies. These results confirm chemotaxonomic differentiation of all subspecies of T. munbyanus.

Background: Rhus pentaphylla Desf. (Anacardiaceae) widely grown in Algeria, is an underutilized plant and remains poorly studied. To investigate for the first time, the chemical composition profile of essential oil and hydrosol extract; besides Total Phenolic (TPC), Flavonoid (TFC) and Condensed Tannins Contents (CTC) of fruits, leaves and roots, the fatty acid composition was assessed. The radical scavenging activity of R. pentaphylla extracts was then evaluated. Methods: Essential oil and hydrosol extract were isolated respectively by hydrodistillation and liquidliquid- extraction from the aerial parts of R. pentaphylla. The antioxidant activity was evaluated using 2,2-Diphenyl-1-Picrylhydrazyl (DPPH) radical and ferric reducing antioxidant power (FRAP). Chemical compositions of various extracts were investigated using Gas Chromatography (GC) and GC-Mass Spectrometry (GC-MS). Results: The results of GC and GC-MS analysis revealed 83 components in essential oil and 75 components in hydrosol extract representing respectively 96.9% and 92.5% of the total extract composition. The main constituents were hexadecanoic acid (31.5%) followed by spathulenol (14.9%) in the oil while the higher amount present in the hydrosol extract was of spathulenol (14.2%). Otherwise, 13 and 18 fatty acids were identified in roots and fruits respectively. The highest levels of TPC and CTC were found in roots extracts while the highest quantity of TFC has been recorded in the leaves extract. Besides, hydrosol extract was able to scavenge DPPH and FRAP free radicals more efficiently than essential oil. Conclusion: R. pentaphylla contains bioactive substances that could be used as a new promising source of antioxidant compounds in different applications.

Background: Tomato is considered a model plant in genetics and is one of the most economically important crops of all those that exist in the world. Several species of fungi are reported on tomato fruit, causing damage both during cultivation and after harvest. Some of the appropriate actions that could be initiated to resolve the problem are to develop and search for new antimicrobial substances isolated from the bioactive natural products, such as essential oils. Aims and Objective: The aim of this work was to determine the chemical composition of essential oils of Ammoides verticillata, Allium sativum and Curcuma longa, to evaluate their in-vitro antifungal activities and in-vivo antifungal effect of essential oils to prevent the diseases caused by tomato. Materials and Methods: The essential oils obtained from aerial parts of plants were analyzed by GC/MS and tested for their antifungal activities against Penicillium expansum, Fusarium solani, Rhizopus stolonifer and Alternaria alternata using the radial growth technique method. The effectiveness in-vivo of the association between Allium sativum and Curcuma longa essential oils was also investigated on tomatoes inoculated by fungi. Results: The essential oil from A. verticilata was mainly composed of phenolic compounds (54.4%), the A. sativum oil was mainly composed of sulfur compounds (91.5%) and C. longa oil was dominated by oxygenated monoterpenes (82.0%). The obtained results in-vitro antifungal revealed that individual essential oils of A. verticillata and A. sativum were more active than the essential oil of C. longa against all screened microorganisms. An important antifungal effect of A. sativum and C. longa essential oils blend was obtained against P. expansum (100%), F. solani (95.2%), R. stolonifer (95.1%) and A. alternata (48.5%). Furthermore, A. sativum and C. longa essential oils blends have demonstrated promising in-vivo antifungal activity to control infection of tomato against P. expansum and R. stolonifer. Conclusion: A. sativum and C. longa essential oil blends can be used as a natural food preservative and alternative to chemical fungicides to protect stored tomato against many phytopathogens.

Background: Atractylis gummifera is a cosmopolitan species that is particularly abundant in the Mediterranean regions. It has been used to treat many diseases, including intestinal parasites, ulcers, snakebite poisoning, hydrops and drowsiness. As part of our research program on natural compounds with biological activities, the objective of this study was to determine for the first time the chemical composition and biological activities of essential oils of Atractylis gummifera during beginning of the vegetative cycle (March), beginning of the flowering stage (April) and full bloom (May/June). Methods: The essential oils were obtained by means of hydrodistillation and its components were analyzed using gas chromatography and mass spectrometry (GC/MS). The antioxidant properties were evaluated using two different methods i) Radical scavenging activity (DPPH) and ii) β-carotene bleaching assay. Whereas, the antifungal activity of the essential oils was investigated against five plant fungi. The fumigation toxicity of essential oils was evaluated against adults of Bactrocera oleae better known as the olive fly. Results: The essential oil produced from the plant taken at the beginning of the vegetative cycle (March) had a high level of non-terpenic aliphatic compounds. On the other hand, the essential oil obtained during the period from the beginning of the flowering stage (April) showed that its proportion of non-terpene compounds decreased and that of sesquiterpene compounds increased. Finally, the essential oils obtained during the period from full bloom (May/June) consisted mainly of acetylene compounds such as carlina oxide and 13-methoxy carlina oxide. The results showed that essential oils from plants at full bloom presented interesting antioxidant and antifungal properties, while essential oil produced from plants at the beginning of the vegetative cycle (Mars) and at the beginning of the flowering stage (April) had better insecticidal activity. Conclusion: The data presented here constitutes new findings in the field of the chemical characterization and biological potential of A. gummifera.

Background: Ammoides verticillata Briq is an aromatic and medicinal herb that has been widely used in folk medicine for treatment of several types of pathologies such as respiratory problems, colds, fever, headache, gastric disorders and renal infections. Objective: Essential oils have been subjected of numerous works for their antimicrobial and insecticidal properties which have been valued by hundreds of publications and patents. The main objective of this work was to evaluate the chemical composition, and the in vitro and in vivo antifungal, and insecticidal properties of essential oil of Ammoides verticillata. Methods: In this work, the air-dried aerial parts of Ammoides verticillata were hydrodistilled in a Clevenger-type apparatus. The essential oil isolated was analyzed using gas chromatography (GC) and mass spectrometry (GC/MS). The in vitro antifungal activity of the essential oil was investigated against four plant fungi using radial growth technique. The effect of the essential oil on disease development of olive caused by Penicillium crustosum and Aspergillus niger in the in vivo conditions. The fumigation test of the essential oil was evaluated against L3 stages, pupas and adults of Bactrocera oleae known as the olive fly. Results: The essential oil of A. verticillata was characterized mainly by carvacrol (44.3%), limonene (19.3%) and p-cymene (19.2%). The result of in vitro antifungal activity of essential oil showed an interesting antifungal inhibition against Alternaria alternata and Fusarium solani strains with percentage inhibition of 89%. Furthermore, oil of A. verticillata has demonstrated promising in vivo antifungal activity to control infections of olives caused by Aspergillus niger and Penicillium crustosum. In addition, the essential oil exhibited fumigation toxicity against Bactrocera oleae with mortality percentage of 100% at 2 μL/L air. Conclusion: The results showed that essential oil of A. verticillata has interesting biological activities, which suggests that oil have the potential to be used as biocide to protect olives of pathogenic fungi and pests.

Background: Bellota species are used to treat various diseases in traditional folk medicine. Objectives: This study aimed to chemically characterize the essential oils and the hydrosol extract and regional specificity of the major components of Ballota nigra essential oil and to evaluate their in vitro and in vivo antifungal activities. Methods: Essential oils were obtained by a Clevenger-type apparatus and analyzed by using Gas Chromatography (GC) and Gas Chromatography Mass Spectroscopy (GC/MS). The antifungal activities were tested to three phytopathogenic stains (Penicillium expansum, Aspergillus niger and Alternaria alternata). Results: Altogether, 38 compounds were identified in the essential oils, representing 92.1-96.8% of the total oil composition. Their main constituents were E-β-caryophyllene (4.8-24.6%), E-β-farnesene (3.3-22.9%), β-bisabolene (7.6-30.2%), α-humulene (2.1-13.3%) and geranyl linalool (1.1-8.2%). The statistical methods deployed confirmed that there is a relation between the essential oil compositions and the harvest locations. Hydrosol extract was constituted by seven components, represented principally by methyl eugenol (75.2%) and caryophyllene oxide (12.5%). The results of in vitro antifungal activity with essential oil and hydrosol extract have shown very interesting antifungal activities on Penicillium expansum and Alternaria alternata strains with percentage reductions up to 80%. Additionally, in in vivo assays, Ballota nigra essential oil and hydrosol extract significantly reduce decay in artificially inoculated tomato by Alternaria alternata. Conclusion: The essential oil and hydrosol extract can be used as a potential source of sustainable eco-friendly botanical fungicides to protect stored tomatoes from pathogens, saprophytic fungi causing bio-deterioration to a variety of food commodities.

AbstractEssential oils (EOs) and hydrosol extract from plants always show a wide range of interesting biological activities. The present study was performed to assess for the first time, the chemical composition and some bioactivities of EO and hydrosol extract from Daphne gnidiumL. growing in Algeria. The chemical characterization of EO and hydrosol extract was carried out by GC/FID and GC/MS analysis. The antioxidant activities were evaluated by DPPH radical scavenging and by FRAP tests. Also, antimicrobial screening of these extracts were performed using the agar disc diffusion test. Ninety-nine components in EO and thirty-two components in hydrosol extract accounting for 95.5 % and 81.4 % of the total extract composition were identified. The main constituents were carvone (12.7 %) followed by spathulenol (11.2 %) in EO, while the major compounds present in the hydrosol extract were carvone (10.9 %) and carvacrol (10.9 %). The results of antioxidant activity of hydrosol extract could be considered more interesting than EO. The data of the antimicrobial assays showed that all strains were sensitive to these extracts where EO displayed a very strong antibacterial activity mainly for E. coli, P. aeruginosaand S. aureusbacteria. Up to date, the current study is the first scientific report of antioxidant and antimicrobial activities as well as the chemical composition of the EO and hydrosol extract of Algerian D. gnidium. The obtained results could promote the potential of D. gnidiumas a promising source of bioactive compounds with a possible application as new natural antioxidant and antimicrobial agents.

ABSTRACTComparative study between the chemical composition of the essential oils of Asteriscus maritimusand Asteriscus spinosusfrom Western Algeria have been investigated. Chemical variability of the essential oils of both species was reported for the first time using gas chromatography/retention indices (GC/RI) and GC-mass spectrometry (GC/MS). A total of 86 compounds were identified in A. maritimuscollective essential oil and 76 compounds in A. spinosuscollective essential oil. Intra-species variations of the chemical compositions of essential oil from eighteen Algerian samples of various locations of both species were also investigated using statistical analysis. A. maritimusessential oils were characterized by T-cadinol (34.2–16.1%), p-cymene (30–15.1%), α-pinene (13.9–2.8%), bornyl acetate (8.7–5.3%) and Z-phytol (7.8–2.4%), as the major compounds. The main compounds of A. spinosuswere α-cadinol (19.8–7.3%), β-pinene (17.6–12.9%), hexadecanoic acid (13.4–4.1%), T-cadinol (10.3–3.5%) and δ-cadinene (8.2–3.9%).