Chemical Composition and Allelopathic Potential of Essential Oils from Citharexylum spinosum L. Grown in Tunisia

Citharexylum spinosum L. (Verbenaceae) also known as Citharexylum quadrangulare Jacq . or Citharexylum fruticosum L. is an exotic tree introduced many years ago in Tunisia, specially used as a street and park ornamental tree. Essential oils (EOs) were obtained by hydrodistillation of the different parts (roots, stems, leaves, flowers and fruits; drupes) collected from trees grown in the area of Monastir (Tunisia). In total, 84 compounds, representing 90.1 – 98.4% of the whole oil composition, were identified by GC‐FID and GC/MS analyses. The root EO was distinguished by its high content in monoterpene hydrocarbons (α‐phellandrene; 30.8%) whereas that obtained from stems was dominated by sesquiterpene hydrocarbons (cuparene; 16.4%). The leaf oil was rich in an apocarotenoid derivative (hexahydrofarnesylacetone; 26%) and an aliphatic hydrocarbon (nonadecane; 14.5%). Flowers oil was rich in esters (2‐phenylethyl benzoate; 33.5%). Finally, drupes oil was rich in oxygenated sesquiterpenes (β‐eudesmol; 33.1%). Flowers oil showed a significant phytotoxic effect against lettuce seeds germination, it induces a total inhibition when tested at 1 mg/ml. Root and shoot elongation seemed to be more affected than germination. The inhibition of the shoot length varied from 3.6% to 100% and that of the root from 16.1% to 100%. The highest inhibition of 100% was detected for flower oil tested at 1 mg/ml. Our in vitro studies suggest a possible and new alternative use of C. spinosum EOs in herbicidal formulations, further experiments involving field conditions are necessary to confirm its herbicidal potential.     

Essential Oil Composition of Phagnalon sordidum (L.) from Corsica,Chemical Variability and Antimicrobial Activity

The chemical composition of Phagnalon sordidum (L.) essential oil was investigated for the first time using gas chromatography and chromatography/mass spectrometry. Seventy‐six compounds, which accounted for 87.9% of the total amount, were identified in a collective essential oil of P. sordidum from Corsica. The main essential oil components were (E)‐β‐caryophyllene (14.4%), β‐pinene (11.0%), thymol (9.0%), and hexadecanoic acid (5.3%). The chemical compositions of essential oils from 19 Corsican locations were investigated. The study of the chemical variability using statistical analysis allowed identifying direct correlation between the three populations of P. sordidum widespread in Corsica and the essential oil compositions they produce. The in vitro antimicrobial activity of P. sordidum essential oil was evaluated and it exhibited a notable activity on a large panel of clinically significant microorganisms.     

Chemical Composition Variability of Essential Oils of Daucus gracilis Steinh. from Algeria

The chemical compositions of 20 Algerian Daucus gracilis essential oils were investigated using GC‐FID, GC/MS, and NMR analyses. Altogether, 47 compounds were identified, accounting for 90 – 99% of the total oil compositions. The main components were linalool ( 18 ; 12.5 – 22.6%), 2‐methylbutyl 2‐methylbutyrate ( 20 ; 9.2 – 20.2%), 2‐methylbutyl isobutyrate ( 10 ; 4.2 – 12.2%), ammimajane ( 47 ; 2.6 – 37.1%), (E)‐β‐ocimene ( 15 ; 0.2 – 12.8%) and 3‐methylbutyl isovalerate ( 19 ; 3.3 – 9.6%). The chemical composition of the essential oils obtained from separate organs was also studied. GC and GC/MS analysis of D. gracilis leaves and flowers allowed identifying 47 compounds, amounting to 92.3% and 94.1% of total oil composition, respectively. GC and GC/MS analysis of D. gracilis leaf and flower oils allowed identifying linalool (22.7%), 2‐methylbutyl 2‐methylbutyrate (18.9%), 2‐methylbutyl isovalerate (13.6%), ammimajane (10.4%), 3‐methylbutyl isovalerate (10.3%), (E)‐β‐ocimene (8.4%) and isopentyl 2‐methylbutyrate (8.1%) as main components. The chemical variability of the Algerian oil samples was studied using statistical analysis, which allowed the discrimination of three main Groups. A direct correlation between the altitudes, nature of soils and the chemical compositions of the D. gracilis essential oils was evidenced.     

Composition and Chemical Variability of the Needle Oil from Pinus halepensis growing in Corsica

The composition of oil samples isolated from needles of Pinus halepensis growing in three locations in Corsica (Saleccia, Capo di Feno, and Tre Padule) has been investigated by combination of chromatographic (GC with retention indices) and spectroscopic (MS and ¹³C‐NMR) techniques. In total, 35 compounds that accounted for 77 – 100% of the whole composition have been identified. α‐Pinene, myrcene, and (E)‐β‐caryophyllene were the major component followed by α‐humulene and 2‐phenylethyl isovalerate. Various diterpenes have been identified as minor components. 47 Oil samples isolated from pine needles have been analyzed and were differentiated in two groups. Oil samples of the first group (15 samples) contained myrcene (M = 28.1 g/100 g; SD = 10.6) and (E)‐β‐caryophyllene (M = 19.0 g/100 g; SD = 2.2) as major components and diterpenes were absent. All these oil samples were isolated from pine needles harvested in Saleccia. Oil samples of the second group (32 samples) contained mostly (E)‐β‐caryophyllene (M = 28.7 g/100 g; SD = 7.9), α‐pinene (M = 12.3 g/100 g; SD = 3.6), and myrcene (M = 11.7 g/100 g; SD = 7.3). All these oil samples were isolated from pine needles harvested in Capo di Feno and Tre Padule.     

Chemical Composition of the Essential Oils from Different Morphological Parts of Pinus cembra L.

The essential oils from needles, twigs, bark, wood, and cones of Pinus cembra were analyzed by GC‐FID, GC/MS, and ¹H‐NMR spectroscopy. More than 130 compounds were identified. The oils differed in the quantitative composition. The principal components of the oil from twigs with needles were α‐pinene (36.3%), limonene (22.7%) and β‐phellandrene (12.0%). The needle oil was dominated by α‐pinene (48.4%), whereas in the oil from bark and in the oil from twigs without needles there were limonene (36.2% and 33.6%, resp.) and β‐phellandrene (18.8% and 17.1%, resp.). The main constituents of the wood oil as well as cone oil were α‐pinene (35.2% and 39.0%, resp.) and β‐pinene (10.4% and 18.9%, resp.). The wood oil and the cone oil contained large amounts of oxygenated diterpenes in comparison with needle, twig, and bark oils.     

Chemical Composition and Antibacterial Activity of Essential Oils from Different Parts of Litsea cubeba

The composition of the essential oils obtained by hydrodistillation of different parts of Litsea cubeba, including roots, stems, leaves, alabastra (flower buds), flowers, and fruits, were investigated by GC (RI) and GC/MS. The antimicrobial activity of the oils was assessed with disc diffusion and microbroth dilution assays. The results showed large variations in the composition among the different oils. The major components in the oils from roots and fruits, from stems, leaves, and alabastra, and from flowers were citral B (neral), β‐phellandrene, and β‐terpinene, respectively. The inhibition zone (DD) and MIC values for the bacterial strains tested, which were all sensitive to the essential oil of L. cubeba, were in the range of 10.1–35.0 mm and 100–1000 μg/ml, respectively. Hence, the oils of the various parts showed moderate activity against the tested bacteria. This investigation showed that the antibacterial activity of L. cubeba was attributed to the essential oils, thus they can be a potential medicinal resource.     

The Chemical Diversity of Eucalyptus spp. Essential Oils from Plants Grown in Brazil

A chemical analysis of essential oils from leaves of eleven Eucalyptus L’Herit taxa, grown in Viçosa, Brazil were carried out. The identification and quantification of essential oils constituents were carried out by GC‐FID and GC/MS. The leaves of E. camaldulensis and E. tereticornis presented the highest oil content (3.00% and 2.30% respectively). In total, 48 compounds were identified in the oils. Higher levels of 1,8‐cineole were found for oils produced by E. microcorys (66.2%), E. urophylla (65.4%) and E. camaldulensis (44.8%) and the hybrid E. urophylla × E. grandis (33.0%). The oil from E. saligna was composed mainly by α‐pinene (92.3%). High concentrations of α‐phellandrene were found in the oils produced by E. camaldulensis (22.9%) and E. robusta (36.6%). The oils from E. grandis and E. pilularis were rich in p‐cymene (59.5% and 46.0%, respectively). Samples with high levels of 1,8‐cineole were classified by principal component analysis (PCA) using the accumulated variance of the PC1 and PC2 into major groups. Other samples were grouped based on their content of p‐cymene; α‐phellandrene, α‐ and β‐eudesmol; α‐pinene. The PCA allowed the separation and classification of samples with the highest levels of different compounds, a procedure that can help in the decision of grouping oils from different sources for industrial use.     

Composition and Antiviral Activity of the Essential Oils of Eryngium alpinum and E. amethystinum

The chemical compositions of the essential oils obtained by hydrodistillation of the aerial parts of Croatian Eryngium alpinum L. and E. amethystinum L. were characterized by GC‐FID and GC/MS analyses. The main components identified were the sesquiterpene β‐caryophyllene (19.7%) in the oil of E. amethystinum and the oxygenated sesquiterpene caryophyllene oxide (21.6%) in the oil of E. alpinum. Overall, 32 and 35 constituents were detected in the essential oils of the aerial parts of E. alpinum and E. amethystinum, respectively, representing 92.4 and 93.1% of the total oil compositions. The essential oils of both Eryngium species were proved to reduce the number of lesions in the local host Chenopodium quinoa infected with cucumber mosaic virus and an associated satellite. This is the first investigation of antiphytoviral activity of essential oils of Eryngium species.     

Chemical Composition and Interpopulation Variability of Essential Oils of Taxus baccata L. from Serbia

The composition of the essential oil of the twigs and needles of Taxus baccata L. from three natural populations in Serbia has been determined by GC/MS analysis. Of the 91 detected compounds, 87 were identified. The most abundant compound classes were aliphatic alcohols, terpenes, aliphatic hydrocarbons, and aliphatic aldehydes, which together comprised ca. 86.92% of the total oil composition. The dominant constituents were oct‐1‐en‐3‐ol (23.48%), (3Z)‐hex‐3‐en‐1‐ol (11.46%; aliphatic alcohols), and myrtenol (11.38%; oxygenated monoterpene). The PCA of 22 selected compounds revealed differentiations of populations based on geographic distribution. The CA showed that Populations I and II from the Dinaric Alps were similar, and that Population III from the Balkan mountain system was distinct. This was the first investigation of interpopulation variability of T. baccata populations based on essential oil composition. The results of this study were compared with those of previous studies concerning volatile compounds produced by Taxus species. The results indicate that the essential oil content of T. baccata populations from this study is unique, mostly resembling the population from southeast Serbia.     

Chemical Composition and Antioxidant Activity of Essential Oils and Methanol Extracts of Different Parts from Juniperus rigida Siebold & Zucc.

The chemical composition and antioxidant activity of essential oils and MeOH extracts of stems, needles, and berries from Juniperus rigida were studied. The results indicated that the yield of essential oil from stems (2.5%) was higher than from needles (0.8%) and berries (1.0%). The gas chromatography/mass spectrometer (GC/MS) analysis indicated that 21, 17, and 14 compounds were identified from stems, needles, and berries essential oils, respectively. Caryophyllene, α‐caryophyllene, and caryophyllene oxide were primary compounds in both stems and needles essential oils. However, α‐pinene and β‐myrcene mainly existed in berries essential oils and α‐ionone only in needles essential oils. The high‐performance liquid chromatography (HPLC) analysis indicated that the phenolic profiles of three parts exhibited significant differences. Needles extracts had the highest content of chlorogenic acid, catechin, podophyllotoxin, and amentoflavone, and for berries extracts, the content of those compounds was the lowest. Meanwhile, three in vitro methods (DPPH, ABTS, and FRAP) were used to evaluate antioxidant activity. Stems essential oil and needles extracts exhibited the powerful antioxidant activity than other parts. This is the first comprehensive study on the different parts of J. rigida. The results suggested that stems and needles of J. rigida are useful supplements for healthy products as new resources.     

Influence of Morphological Variability and Habitat on the Chemical Composition of Essential Oils of an Algerian Endemic Origanum Species (Origanum floribundum Munby)

The genus Origanum L. (Lamiaceae) enjoys a socioeconomic interest and constitutes one of the most popular spices. In the literature, the study of this taxon is limited mainly to the chemical composition, antimicrobial, antifungal, and antioxidant activities of the essential oils. In Algeria, few works have been done in this area, including the endemic and rare species: Origanum floribundum Munby . In this study, our contribution highlights the influence of the ecological parameters and of the variation of morphological traits on the chemical composition and the antioxidant activity of the essential oils of six populations. The major oils constituents are carvacrol, γ‐terpinene, and p‐cymene with carvacrol predominance (31.8 – 60.8%) in over five populations (MS1 – MS4 and MS6). However, the population of Ain Terraeur (MS5) of which individuals present a foliar polymorphism, distinguishes itself by p‐cymene predominance (42.6%). This would denote a new chemotype and/or variety which seem well differentiated on the dendrogram of the Ascending Hierarchical Classification (A.H.C) and its foliar morphology. The antioxidant activity of the six samples evaluated by the scavenging activity of free radicals DPPH^? and ABTS^?+ showed a potent efficiency for the sample with foliar polymorphism population (IC₅₀ = 51.6 ± 0.31 and 12.71 ± 0.37 μg/ml, respectively).     

Chemical Variability,Antioxidant and Antifungal Activities of Essential Oils and Hydrosol Extract of Calendula arvensis L. from Western Algeria

The chemical composition of the essential oils and hydrosol extract from aerial parts of Calendula arvensis L. was investigated using GC‐FID and GC/MS. Intra‐species variations of the chemical compositions of essential oils from 18 Algerian sample locations were investigated using statistical analysis. Chemical analysis allowed the identification of 53 compounds amounting to 92.3 – 98.5% with yields varied of 0.09 – 0.36% and the main compounds were zingiberenol 1 (8.7 – 29.8%), eremoligenol (4.2 – 12.5%), β‐curcumene (2.1 – 12.5%), zingiberenol 2 (4.6 – 19.8%) and (E,Z)‐farnesol (3.5 – 23.4%). The study of the chemical variability of essential oils allowed the discrimination of two main clusters confirming that there is a relation between the essential oil compositions and the harvest locations. Different concentrations of essential oil and hydrosol extract were prepared and their antioxidant activity were assessed using three methods (2,2‐diphenyl‐1‐picrylhydrazyl, Ferric‐Reducing Antioxidant Power Assay and β‐carotene). The results showed that hydrosol extract presented an interesting antioxidant activity. The in vitro antifungal activity of hydrosol extract produced the best antifungal inhibition against Penicillium expansum and Aspergillus niger, while, essential oil was inhibitory at relatively higher concentrations. Results showed that the treatments of pear fruits with essential oil and hydrosol extract presented a very interesting protective activity on disease severity of pears caused by P. expansum.     

Chemical Composition of Volatiles; Antimicrobial,Antioxidant and Cholinesterase Inhibitory Activity of Chaerophyllum aromaticum L. (Apiaceae) Essential Oils and Extracts

The present study reports the chemical composition of the headspace volatiles (HS) and essential oils obtained from fresh Chaerophyllum aromaticum root and aerial parts in full vegetative phase, as well as biological activities of their essential oils and MeOH extracts. In HS samples, the most dominant components were monoterpene hydrocarbons. On the other hand, the essential oils consisted mainly of sesquiterpenoids, representing 73.4% of the root and 63.4% of the aerial parts essential oil. The results of antibacterial assay showed that the aerial parts essential oil and MeOH extract have no antibacterial activity, while the root essential oil and extract showed some activity. Both of the tested essential oils exhibited anticholinesterase activity (47.65% and 50.88%, respectively); MeOH extract of the root showed only 8.40% inhibition, while aerial part extract acted as an activator of cholinesterase. Regarding the antioxidant activity, extracts were found to be more effective than the essential oils.     

Chemical Diversity and Antimicrobial Activity of Salvia multicaulis Vahl Essential Oils

The chemical compositions and antimicrobial activities of the essential oils (EOs) of aerial parts of Salvia multicaulis Vahl , collected during the same week from two different Lebanese regions, were investigated. The EOs were obtained by hydrodistillation using a Clevenger‐type apparatus and characterized by GC and GC/MS analyses. The minimum inhibitory concentrations of these EOs were determined against one Gram‐negative and two Gram‐positive bacteria, one yeast, and five dermatophytes using the broth microdilution technique. One EO was notably active against Staphylococcus aureus, methicillin‐resistant S. aureus, and all of the Trichophyton species tested. Nerolidol was found to be the major compound in the active oil; nerolidol was also absent from the inactive oil. This study demonstrated that nerolidol shows antimicrobial activity and therefore significantly contributes to the antimicrobial potential of the oil. The chemical diversity of worldwide S. multicaulis EOs was analyzed, revealing that the EOs of this study belong to two different chemotypes found in the literature. The nerolidol chemotype appears to be restricted to Lebanon, and it can be used as antimicrobial agent against external bacterial and fungal infections.     

Composition and Chemical Variability of Ivoirian Polyalthia oliveri Leaf Oil

The chemical composition of 45 essential oil samples isolated from the leaves of Polyalthia oliveri harvested in three Ivoirian forests was investigated by GC‐FID (retention indices measured on two columns of different polarities), and by ¹³C‐NMR, following a method developed in our laboratory. In total, 41 components were identified. The content of the main components varied drastically from sample to sample: (E)‐β‐caryophyllene (1.2 – 50.8%), α‐humulene (0.6 – 47.7%), isoguaiene (0 – 27.9%), alloaromadendrene (0 – 24.7%), germacrene B (0 – 18.3%), δ‐cadinene (0.4 – 19.3%), and β‐selinene (0.2 – 18.5%). The analysis of six oil samples selected in function of their chromatographic profiles is reported in detail. The 45 oil compositions were submitted to hierarchical cluster and principal components analysis, which allowed the distinction of three groups within the oil samples. The compositions of the oils from group I (15 samples) and II (12 samples) were dominated by (E)‐β‐caryophyllene and α‐humulene, respectively. Oil samples of group III (18 samples) needed to be partitioned into four subgroups III.1–III.4 whose compositions were dominated by alloaromadenrene, isoguaiene, germacrene B, and δ‐cadinene, respectively.     

Essential Oils of Micromeria dalmatica Benth., a Balkan Endemic Species of Section Pseudomelissa

The essential oils of 13 Greek populations of Micromeria dalmatica, a Balkan endemic species and member of the section Pseudomelissa, were examined for the first time. Among the studied populations, two main oil types could be distinguished. Type I was found to be rich in β‐pinene, limonene, and germacrene D (accounting for 55.6–70.2% of the total oil), and Type II was characterized by the preponderance of p‐menthane compounds (accounting for 64.2–89.9% of the oil). The latter oil type could be further divided into two subtypes, one comprising oils with predominance of piperitenone and piperitenone oxide and another composed of oils containing high proportions of pulegone, menthone, and isomenthone. The abundance of p‐menthane compounds is a common feature of the oils of all members of the section Pseudomelissa studied to date. However, the existence of oils of Type I has not been previously reported for M. dalmatica, neither for other members of the section Pseudomelissa.     

Chemical Composition and Antimicrobial Activity of the Essential Oil of Juniperus excelsa M.Bieb. Growing Wild in Lebanon

The essential oils (EOs) isolated from the leaves and twigs of Juniperus excelsa M.Bieb . growing wild in Lebanon were characterized, and their antimicrobial activity and antiradical capacity were evaluated. The EOs were obtained by hydrodistillation using a Clevenger‐type apparatus and characterized by GC and GC/MS analyses. The antimicrobial activity was evaluated by determining minimal inhibitory concentrations (MICs) against a Gram‐positive and a Gram‐negative bacterium, a yeast, and a dermatophyte with the broth microdilution technique. A total of 28 constituents was identified and accounted for 90.1 and 95.6% of the twig and leaf EO composition, respectively. Both EOs were essentially composed of monoterpene hydrocarbons (46.7 and 59.6% for twig and leaf EOs, resp.) and sesquiterpenes (39.4 and 32.1%, resp.). The main components were α‐pinene, α‐cedrol, and δ‐car‐3‐ene. The J. excelsa EOs did not show any antiradical potential, but revealed interesting in vitro antimicrobial activities against Staphylococcus aureus and Trichophyton rubrum (MICs of 64 and 128 μg/ml, resp.). The three major compounds were tested separately and in combination according to their respective amounts in the oil. δ‐Car‐3‐ene was the most active component and is undoubtedly one of the constituents driving the antifungal activity of J. excelsa essential oil, even though synergies are probably involved.     

The Essential Oil of Bupleurum fruticosum L. from Corsica: A Comprehensive Study

A detailed analysis of Bupleurum fruticosum oil was carried out by combination of GC (RI), GC/MS, and ¹³C‐NMR analyses. After fractionation by column chromatography, 34 components accounting for 97.8% of the oils were identified. The main component was β‐phellandrene (67.7%), followed by sabinene (9.3%), and limonene (5.6%). The evolution of the chemical composition according to the stages of development of the plant was investigated as well as the composition of leaf, twig, and flower oils. A solvent‐free microwave extraction (SFME) of aerial parts was carried out and the composition of the extract compared with that of the essential oil. Finally, 57 oil samples isolated from aerial parts of individual plants, collected all around Corsica, were analyzed, and the data were submitted to statistical analysis. Although the contents of the main components varied, only one group emerged, accompanied with some atypical compositions.     

Chemical Composition and Biological Prospects of Essential Oils and Extracts of Aphyllocladus spartioides Growing in Northwest Argentina

Aphyllocladus spartioides Wedd . is a native and aromatic herb used in traditional medicine, however it is still poorly investigated. In this work, the volatile profile of A. spartioides growing in Hornillos‐Northwest Argentina was determined by GC/MS/FID and the phenolic compounds of hydroethanolic and decoction extracts were analyzed by HPLC‐DAD. The antibacterial potential, antioxidant activity and α‐glucosidase inhibition activity were checked by in vitro assays. The volatile profile allowed the identification of 68 compounds, being α‐pinene and cadinene the main ones. Eighteen phenolics were identified, isorhamnetin derivatives and different phenolic acid derivatives were found in higher amounts, mainly in the hydroethanolic extract. A concentration‐dependent activity was noticed against DPPH^·, , and α‐glucosidase, these activities being reported for the first time. Hydroethanolic extract was most active against DPPH^·, ^·NO and α‐glucosidase (IC₅₀ = 79, 206 and 181 μg/ml). Decoction extract proved to be better against (IC₅₀ = 20 μg/ml). Regarding the antibacterial activity, hydroethanolic extract was more active compared with decoction and essential oil. MICs of 0.3 – 0.6 mg/ml were obtained against Staphylococcus aureus, Bacillus cereus, and Micrococcus luteus. Results suggest that the extracts of A. spartioides from Northwest Argentina may be interesting to use as a source of natural antioxidants/antimicrobials for pharmaceutical incorporations or food supplementation.     

Inhibitory Activity and Chemical Characterization of Daucus carota subsp. maximus Essential Oils

The essential oils (EOs) of green seeds from Daucus carota subsp. maximus growing wild in Pantelleria Island (Sicily, Italy) were characterized. EOs were extracted by steam distillation, examined for their inhibitory properties against food‐borne Gram‐positive and Gram‐negative bacteria and analyzed for the chemical composition by gas chromatography (GC) and mass spectrometry (MS). Undiluted EOs showed a large inhibition spectrum against Gram‐positive strains and also vs. Acinetobacter spp. and Stenotrophomonas maltophilia. The minimum inhibition concentration (MIC) was in the range 1.25 – 2.50 μl/ml for the most sensitive strains. The chemical analysis indicated that D. carota subsp. maximus EOs included 34 compounds (five monoterpene hydrocarbons, six oxygenated monoterpenes, 14 sesquiterpene hydrocarbons, four oxygenated sesquiterpenes, camphorene and four other compounds), accounting for 95.48% of the total oil, and that the major chemicals were carotol, β‐bisabolene, and isoelemicin.