Chemical Variability of Cleistopholis patens (Benth.) Engl. et Diels Leaf Oil from Ivory Coast

The chemical composition of 48 leaf oil samples isolated from individual plants of Cleistopholis patens (Benth .) Engl. et Diels harvested in four Ivoirian forests was investigated by GC‐FID (determination of retention indices), GC/MS, and ¹³C‐NMR analyses. The main components identified were β‐pinene (traces–59.1%), sabinene (traces–54.2%), (E)‐β‐caryophyllene (0.3–39.3%), linalool (0.1–38.5%), (E)‐β‐ocimene (0.1–33.2%), germacrene D (0.0–33.1%), α‐pinene (0.1–32.3%), and germacrene B (0–21.2%). The 48 oil compositions were submitted to hierarchical clustering and principal components analyses, which allowed the distinction of three groups within the oil samples. The oil composition of the major group (Group I, 33 samples) was dominated by (E)‐β‐caryophyllene and linalool. The oils of Group II (eight samples) contained mainly β‐pinene and α‐pinene, while those of Group III (seven samples) were dominated by sabinene, limonene, and β‐phellandrene. Moreover, the compositions of the Ivoirian C. patens leaf oils differed from those of Nigerian and Cameroonian origins.     

Composition and Chemical Variability of Cleistopholis patens Trunk Bark Oil from Côte d'Ivoire

The chemical composition of trunk bark oil from Cleistopholis patens (Benth .) Engl . & Diels , growing wild in Côte d'Ivoire, has been investigated by GC (FID) in combination with retention indices, GC/MS and ¹³C‐NMR. Moreover, one oil sample has been subjected to CC and all the fractions analyzed by GC (RI) and ¹³C‐NMR. In total, 61 components have been identified, including various sesquiterpene esters scarcely found in essential oils. ¹³C‐NMR was particularly efficient for the identification of a component not eluted on GC and for the quantification of heat‐sensitive compounds. Then, 36 oil samples, isolated from trunk bark harvested in six Ivoirian forests have been analyzed. The content of the main components varied drastically from sample to sample: (E)‐β‐caryophyllene (0.4 – 69.1%), β‐pinene (0 – 57%), α‐phellandrene (0 – 33.2%), α‐pinene (0.1 – 30.6%), β‐elemol (0.1 – 29.9%), germacrene D (0 – 25.4%), juvenile hormone III (0 – 22.9%), germacrene B (0 – 20.6%) and sabinene (tr‐20.3%). Statistical analysis, hierarchical clustering and principal components analysis, carried out on the 36 compositions evidenced a fair chemical variability of the stem bark oil of this species. Indeed, three clusters have been distinguished: the composition of group I (ten samples) was dominated by β‐pinene and α‐pinene, group II (nine samples) was represented by α‐phellandrene and p‐cymene and group III (16 samples) by β‐elemol. A sample displayed an atypical composition dominated by (E)‐β‐caryophyllene.     

Chemical Variability of Xylopia quintasii Engl. & Diels Leaf Oil from Côte d'Ivoire

The chemical composition of 42 essential‐oil samples isolated from the leaves of Xylopia quintasii harvested in three Ivoirian forests was investigated by GC‐FID, including the determination of retention indices (RIs), and by ¹³C‐NMR analyses. In total, 36 components accounting for 91.9–92.6% of the oil composition were identified. The content of the main components varied drastically from sample to sample: (E)‐β‐caryophyllene (0.9–56.9%), (Z)‐β‐ocimene (0.3–54.6%), β‐pinene (0.8–27.9%), α‐pinene (0.1–22.8%), and furanoguaia‐1,4‐diene (0.0–17.6%). The 42 oil compositions were submitted to hierarchical cluster and principal components analysis, which allowed the distinction of three groups within the oil samples. The composition of the oils of the major group (22 samples) was dominated by (E)‐β‐caryophyllene. The oils of the second group (12 samples) contained β‐pinene and α‐pinene as the principal compounds, while the oils of the third group (8 samples) were dominated by (Z)‐β‐ocimene, germacrene D, (E)‐β‐ocimene, and furanoguaia‐1,4‐diene. The oil samples of Group I and II came from clay‐soil forests, while the oil samples belonging to Group III were isolated from leaves harvested in a sandy‐soil forest.     

Chemical Variability of the Leaf Essential Oil of Xylopia aethiopica (Dunal) A.Rich. from Côte d'Ivoire

The chemical composition of 48 essential‐oil samples isolated from the leaves of Xylopia aethiopica harvested in six Ivoirian forests was investigated by GC‐FID and ¹³C‐NMR analyses. In total, 23 components accounting for 82.5–96.1% of the oil composition were identified. The composition was dominated by the monoterpene hydrocarbons β‐pinene (up to 61.1%) and α‐pinene (up to 18.6%) and the sesquiterpene hydrocarbon germacrene D (up to 28.7%). Hierarchical cluster and principal component analyses allowed the distinction of two groups on the basis of the β‐pinene and germacrene D contents. The chemical composition of the oils of Group I (38 oil samples) was clearly dominated by β‐pinene, while those of Group II (10 samples) were characterized by the association of β‐pinene and germacrene D. The leaves collected in the four inland forests produced β‐pinene‐rich oils (Group I), while the oil samples belonging to Group II were isolated from leaves harvested in forests located near the littoral.     

Volatile Compounds in Fruits of Peucedanum cervaria (Lap.) L.

The volatile compounds from Peucedanum cervaria (Lap. ) L. were obtained by hydrodistillation (HD) and headspace solid‐phase microextraction techniques (HS‐SPME), and then analyzed by GC/MS methods. The composition of samples from a botanical garden was compared with plants collected in the wild. The main compounds of the essential oils of P. cervaria were identified as α‐pinene, sabinene, and β‐pinene (more than 80% of oil). The content of β‐myrcene, limonene+β‐phellandrene, and germacrene D was higher than 1%. The in vitro antibacterial activity of the essential oil was evaluated by the agar dilution method against ten reference strains of Gram‐positive and Gram‐negative bacteria.     

Variation in Chemical Composition and Antibacterial Activity of the Essential Oil of Wild Populations of Phlomis olivieri

Various species of the genus Phlomis have been reported to produce metabolites demonstrating significant pharmacological efficiency. In this study, the essential oils from twelve populations of Phlomis olivieri collected from natural habitats were investigated for their chemical components. The hydrodistillated essential oil analyzed by GC‐FID and GC/MS. Analyses revealed 27 compounds, constituting 90.52 – 98.51% of the essential oils. Results indicated that the major components of the essential oils from various populations of P. olivieri were germacrene D (26.54 – 56.41%), bicyclogermacrene (6.38 – 30.55%), β‐caryophyllene (5.32 – 24.52%) and α‐pinene (1.29 – 15.53%). Principal component analyses (PCA) was used to identify any geographical variations in essential oil composition. Notably, three groups of Iranian P. olivieri populations were determined according to the major compounds. Results of the in vitro antibacterial activity indicated that P. olivieri essential oils showed good inhibitory activities against bacteria, especially Bacillus subtilis. The results of this study gave new insights for cultivation and industrial uses of P. olivieri in Iran.     

Essential‐Oil Composition of the Needles Collected from Natural Populations of Macedonian Pine (Pinus peuce Griseb.) from the Scardo‐Pindic Mountain System

The needle‐terpene profiles of two natural Pinus peuce populations from the Scardo‐Pindic mountain system (Mt. O?ljak and Mt. Pelister) were analyzed. Among the 90 detected compounds, 87 were identified. The dominant constituents were α‐pinene (45.5%), germacrene D (11.1%), β‐pinene (10.8%), and camphene (10.3%). The following eight additional components were found to be present in medium‐to‐high amounts (0.5–10%): bornyl acetate (5.0%), β‐phellandrene (3.4%), β‐caryophyllene (2.9%), β‐myrcene (0.9%), germacrene D‐4‐ol (0.9%), tricyclene (0.7%), (E)‐hex‐2‐enal (0.7%), and bicyclogermacrene (0.6%). Although the general needle‐terpene profiles of the populations from Mt. O?ljak and Mt. Pelister were found to be similar to those of the populations from Zeletin, Sjekirica, and Mokra Gora (Dinaric Alps), principle component analysis (PCA) of eight terpenes (α‐pinene, β‐myrcene, α‐terpinolene, bornyl acetate, α‐terpinyl acetate, β‐caryophyllene, trans‐β‐farnesene, and germacrene D) in 139 tree samples suggested a divergence between the two population groups, i.e., the samples from the Scardo‐Pindic mountain system and those from the Dinaric Alps. Genetic analysis of the β‐pinene content demonstrated a partial divergence between the two geographical groups. The profiles of both population groups differed from those published for populations from the Balkan‐Rhodope mountains system (literature results), which were characterized by high contents of bornyl acetate and citronellol (Greek populations) or δ‐car‐3‐ene (Bulgarian populations).     

Population Variability of Essential Oils of Pinus heldreichii from the Scardo‐Pindic Mountains Ošljak and Galičica

The needle‐terpene profiles of two natural Pinus heldreichii populations from Mts. O?ljak and Gali?ica (Scardo‐Pindic mountain system) were analyzed. Among the 68 detected compounds, 66 were identified. The dominant constituents were germacrene D (28.7%), limonene (27.1%), and α‐pinene (16.2%). β‐Caryophyllene (6.9%), β‐pinene (5.2%), β‐myrcene (2.3%), pimaric acid (2.0%), α‐humulene (1.2%), and seven additional components were found to be present in medium‐to‐high amounts (0.5–10%). Although the general needle‐terpene profile of the population from Gali?ica was similar to those of the populations from Lov?en, Zeletin, Bjelasica, and Zlatibor‐Pe?ter (belonging to the Dinaric Alps), the principle‐component analysis (PCA) of seven terpenes (β‐myrcene, limonene, β‐elemene, β‐caryophyllene, α‐humulene, δ‐cadinene, and germacrene D‐4‐ol) in 121 tree samples suggested a partial divergence in the needle‐terpene profiles between the populations from the Scardo‐Pindic mountain system and the Dinaric Alps. According to previously reported data, the P. heldreichii samples from the Balkan‐Rhodope mountains lack β‐caryophyllene and germacrene D, but contain γ‐muurolene in their terpene profile. Differences in the terpene composition between populations growing in the three above‐mentioned mountain systems were compared and discussed.     

Juniperus phoenicea var. turbinata (Guss.) Parl. Leaf Essential Oil Variability in the Balkans

In the present work, the leaf essential oil from 97 individuals of Juniperus phoenicea var. turbinata (Guss .) Parl . from the Balkan Peninsula was analyzed. The essential oil was dominated by monoterpene hydrocarbons (45.5 – 71.8%), of which α‐pinene was the most abundant in almost all of the samples (38.2 – 55.8%). Several other monoterpenes and sesquiterpenes were also present in relatively high abundances in samples such as myrcene, δ‐3‐carene, β‐phellandrene, α‐terpinyl acetate, (E)‐caryophyllene and germacrene D. Multivariate statistical analysis suggested the existence of three possible chemotypes based on the abundance of the four components. Even though the intrapopulation variability was high, discriminant analysis (DA) was able to separate populations. DA showed high separation between western and eastern populations but also grouped geographically closer populations along the west Balkan shoreline. The potential influence of the climate on the composition of the essential oil was also studied.     

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 and Antipathogenic Activity of Artemisia annua Essential Oil from Romania

The essential oil extracted by hydrodistillation from Romanian Artemisia annua aerial parts was characterized by GC/MS analysis, which allowed the identification of 94.64% of the total oil composition. The main components were camphor (17.74%), α‐pinene (9.66%), germacrene D (7.55%), 1,8‐cineole (7.24%), trans‐β‐caryophyllene (7.02%), and artemisia ketone (6.26%). The antimicrobial activity of this essential oil was evaluated by determining the following parameters: minimal inhibitory concentration (MIC), minimal bactericidal concentration (MBC), minimal fungicidal concentration (MFC), and minimal biofilm eradication concentration (MBEC). Moreover, the soluble virulence factors were quantified with different biochemical substrates incorporated in the culture media. The reference and resistant, clinical strains proved to be susceptible to the A. annua oil, with MICs ranging from 0.51 to 16.33 mg/ml. The tested essential oil also showed good antibiofilm activity, inhibiting both the initial stage of the microbial cell adhesion to the inert substratum and the preformed mature biofilm. When used at subinhibitory concentrations, the essential oil proved to inhibit the phenotypic expression of five soluble virulence factors (hemolysins, gelatinase, DNase, lipases, and lecithinases). Briefly, the present results showed that the A. annua essential oil contained antimicrobial compounds with selective activity on Gram‐positive and Gram‐negative bacterial strains as well as on yeast strains and which also interfere with the expression of cell‐associated and soluble virulence factors.     

Composition, and antimicrobial and remarkable antiprotozoal activities of the essential oil of rhizomes of Aframomum sceptrum K. Schum. (Zingiberaceae)

The essential oil from the rhizomes of Aframomum sceptrum (Zingiberaceae) was analyzed by GC/MS, and its major constituents were found to be β‐pinene (12.7%), caryophyllene oxide (10.0%), and cyperene (6.0%). The oil was also evaluated for antimicrobial activities, in comparison with β‐pinene, caryophyllene oxide, and the leaf essential oil of Melaleuca alternifolia (Myrtaceae). The A. sceptrum essential oil exhibited bacteriostatic activity against the Gram‐positive bacteria Bacillus subtilis, Staphylococcus epidermidis, and S. aureus, but not against Gram‐negative bacteria. Moreover, it showed mild fungicidal activity against Candida albicans and Aspergillus fumigates, and remarkable antiprotozoal activity against Trypanosoma brucei brucei (MLC of 1.51 μl/ml) and Trichomonas vaginalis (IC₅₀ of 0.12±0.02 and MLC of 1.72 μl/ml).     

Comparison of Chemical Composition of the Essential Oils from Different Botanical Organs of Pinus mugo Growing in Poland

The essential oils from needles, twigs, bark, wood, cones and young shoots of Pinus mugo were analyzed by GC, 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 3‐carene (23.8 %), myrcene (22.3 %), and α‐pinene (10.3 %). The needle oil contained mainly α‐pinene (18.6 %), 3‐carene (11.3 %), and bornyl acetate (8.3 %). The oils from twigs without needles, young shoots, bark, and wood were dominated by 3‐carene (28.6 %, 15.0 %, 18.5 %, and 34.6 %, respectively) and myrcene (23.4 %, 24.0 %, 24.6 %, and 9.4 %, respectively). In the cone oil (E)‐β‐caryophyllene was the main constituent (24.0 %).     

Essential Oil Composition of Centaurea atropurpurea and Centaurea orientalis Inflorescences from the Central Balkans – Ecological Significance and Taxonomic Implications

The essential oil composition of Centaurea atropurpurea and Centaurea orientalis flowering heads (capitula) from Central Balkans have been determined by GC‐FID and GC/MS analyses. In total, 121 compounds were identified, representing on average 97.7% of the oil composition. In all samples, sesquiterpenes were most abundant group, representing 53.9 – 74.0% of the total oil. Sesquiterpene hydrocarbons dominated in all studied populations of C. orientalis and C. atropurpurea, except C. atropurpurea f. flava in which essential oil was characterized with high level of oxygenated sesquiterpenes. The dominant components differed between species, and also between typical C. atropurpurea and C. atropurpurea f. flava. The most abundant compounds of essential oil of C. orientalis were germacrene D and α‐cadinol. In C. atropuruprea, germacrene D and β‐caryophyllene were the most abundant, while caryophyllene oxide and β‐caryophyllene were dominant in C. atropurpurea f. flava oil. Taxonomical and ecological implications are further discussed.     

Chemical Variability of the Essential Oil of Juniperus phoenicea var. turbinata from Algeria

The chemical composition of 50 samples of leaf oil isolated from Algerian Juniperus phoenicea var. turbinata L. harvested in eight locations (littoral zone and highlands) was investigated by GC‐FID (in combination with retention indices), GC/MS, and ¹³C‐NMR analyses. The composition of the J. phoenicea var. turbinata leaf oils was dominated by monoterpenes. Hierarchical cluster and principal component analyses confirmed the chemical variability of the leaf oil of this species. Indeed, three clusters were distinguished on the basis of the α‐pinene, α‐terpinyl acetate, β‐phellandrene, and germacrene D contents. In most oil samples, α‐pinene (30.2–76.7%) was the major compound, associated with β‐phellandrene (up to 22.5%) and α‐terpinyl acetate (up to 13.4%). However, five out of the 50 samples exhibited an atypical composition characterized by the predominance of germacrene D (16.7–22.7%), α‐pinene (15.8–20.4%), and α‐terpinyl acetate (6.1–22.6%).     

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.     

Chemical Composition of the Essential Oil and Diethyl Ether Extract of Trinia glauca (L.) Dumort. (Apiaceae) and the Chemotaxonomic Significance of 5‐O‐Methylvisamminol

Analyses by GC, GC/MS, and NMR spectroscopy (1D‐ and 2D‐experiments) of the essential oil and Et₂O extract of Trinia glauca (L .) Dumort . (Apiaceae) aerial parts allowed a successful identification of 220 constituents, in total. The major identified compounds of the essential oil were (Z)‐falcarinol (10.6%), bicyclogermacrene (8.0%), germacrene D (7.4%), δ‐cadinene (4.3%), and β‐caryophyllene (3.2%), whereas (Z)‐falcarinol (47.2%), nonacosane (7.4%), and 5‐O‐methylvisamminol (4.0%) were the dominant constituents of the extract of T. glauca. One significant difference between the compositions of the herein and the previously analyzed T. glauca essential oils (only two reports) was noted. (Z)‐Falcarinol was the major constituent in our case, whereas germacrene D (14.4 and 19.6%) was the major component of the previously studied oils. Possible explanations for this discrepancy were discussed. 5‐O‐Methylvisamminol, a (furo)chromone identified in the extract of T. glauca, has a limited occurrence in the plant kingdom and is a possible excellent chemotaxonomic marker (family and/or subfamily level) for Apiaceae.     

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.     

Chemical Composition of Hypericum rumeliacum Boiss. Essential Oil. A New Chemotype of This Pharmacologically Valuable Species?

Analysis by GC and GC/MS of the essential‐oil samples obtained from dry above‐ground parts of Hypericum rumeliacum Boiss . (collected in the flowering and fruit‐forming vegetative stages) allowed the identification of 212 components in total, comprising ≥97.8% of the total oil composition. In the flowering phase, the major identified volatile compounds were undecane (6.6%), dodecanal (10.8%), and germacrene D (14.1%), whereas α‐pinene (7.3%), β‐pinene (26.1%), (Z)‐β‐ocimene (8.5%), (E)‐β‐ocimene (10.2%), bicyclogermacrene (7.7%), and germacrene D (15.1%) were dominant in the fruit‐forming phase. Some of the minor constituents found in the studied oil samples (e.g., a homologous series of four 6‐alkyl‐5,6‐dihydro‐2H‐pyran‐2‐ones, i.e., massoia dodeca‐, trideca‐, tetradeca‐, and hexadecalactones) have a restricted occurrence in the Plant Kingdom, and their presence in Hypericum L. spp. has not been previously reported. The chemical compositions of the herein studied additional 34 oils obtained from selected Hypericum taxa were compared using multivariate statistical analysis (agglomerative hierarchical cluster analysis and principal component analysis). The results of these statistical analyses could not be used to either confirm or discard the existence of different H. rumeliacum chemotypes. However, they have implied that the volatile profile of this plant species is determined by the stage of its phenological development.     

Chemical Diversity among the Essential Oils of Wild Populations of Stachys lavandulifolia Vahl (Lamiaceae) from Iran

The variation of the essential‐oil composition among ten wild populations of Stachys lavandulifolia Vahl (Lamiaceae), collected from different geographical regions of Iran, was assessed by GC‐FID and GC/MS analyses, and their intraspecific chemical variability was determined. Altogether, 49 compounds were identified in the oils, and a relatively high variation in their contents was found. The major compounds of the essential oils were myrcene (0.0–26.2%), limonene (0.0–24.5%), germacrene D (4.2–19.3%), bicyclogermacrene (1.6–18.0%), δ‐cadinene (6.5–16.0%), pulegone (0.0–15.1%), (Z)‐hex‐3‐enyl tiglate (0.0–15.1%), (E)‐caryophyllene (0.0–12.9), α‐zingiberene (0.2–12.2%), and spathulenol (1.6–11.1%). For the determination of the chemotypes and the chemical variability, the essential‐oil components were subjected to cluster analysis (CA). The five different chemotypes characterized were Chemotype I (germacrene D/bicyclogermacrene), Chemotype II (germacrene D/spathulenol), Chemotype III (limonene/δ‐cadinene), Chemotype IV (pulegone), and Chemotype V (α‐zingiberene). The high chemical variation among the populations according to their geographical and bioclimatic distribution imposes that conservation strategies of populations should be made appropriately, taking into account these factors. The in situ and ex situ conservation strategies should concern all populations representing the different chemotypes.