Variation of the Chemical Composition and Antimicrobial Activity of the Essential Oils of Natural Populations of Tunisian Daucus carota L. (Apiaceae)

The essential oils of Daucus carota L. (Apiaceae) seeds sampled from ten wild populations spread over northern Tunisia were characterized by GC‐FID and GC/MS analyses. In total, 36 compounds were identified in the D. carota seed essential oils, with a predominance of sesquiterpene hydrocarbons in most samples (22.63–89.93% of the total oil composition). The main volatile compounds identified were β‐bisabolene (mean content of 39.33%), sabinene (8.53%), geranyl acetate (7.12%), and elemicin (6.26%). The volatile composition varied significantly across the populations, even for oils of populations harvested in similar areas. The chemometric principal component analysis and the hierarchical clustering identified four groups, each corresponding to a composition‐specific chemotype. The in vitro antimicrobial activity of the isolated essential oils was preliminarily evaluated, using the disk‐diffusion method, against one Gram‐positive (Staphylococcus aureus) and two Gram‐negative bacteria (Escherichia coli and Salmonella typhimurium), as well as against a pathogenic yeast (Candida albicans). All tested essential oils exhibited interesting antibacterial and antifungal activities against the assayed microorganisms.     

Chemotype Diversity of Indigenous Dalmatian Sage (Salvia officinalis L.) Populations in Montenegro

To identify how many chemotypes of Salvia officinalis exist in Montenegro, the chemical composition of the essential oils of 12 wild‐growing populations was determined by GC‐FID and GC/MS analyses. Among the 40 identified constituents, the most abundant were cis‐thujone (16.98–40.35%), camphor (12.75–35.37%), 1,8‐cineol (6.40–12.06%), trans‐thujone (1.5–10.35%), camphene (2.26–9.97%), borneol (0.97–8.81%), viridiflorol (3.46–7.8%), limonene (1.8–6.47%), α‐pinene (1.59–5.46%), and α‐humulene (1.77–5.02%). The composition of the essential oils under study did not meet the ISO 9909 requirements, while the oils of populations P02–P04, P09, and P10 complied with the German Drug Codex. A few of the main essential‐oil constituents appeared to be highly intercorrelated. Strong positive correlations were observed between α‐pinene and camphene, camphene and camphor, as well as between cis‐thujone and trans‐thujone. Strong negative correlations were evidenced between cis‐thujone and α‐pinene, cis‐thujone and champhene, cis‐thujone and camphor, as well as between trans‐thujone and camphene. Multivariate analyses allowed the grouping of the populations into three distinct chemotypes, i.e., Chemotype A, rich in total thujones, Chemotype B, with intermediate contents of thujones, α‐pinene, camphene, and camphor and high borneol contents, and Chemotype C, rich in camphor, camphene, and α‐pinene. The chemotypes did not significantly differ in the total essential‐oil content and the cis/trans‐thujone ratio.     

Essential Oils and Chemical Diversity of Southeast European Populations of Salvia officinalis L.

The essential oils of 25 populations of Dalmatian sage (Salvia officinalis L.) from nine Balkan countries, including 17 indigenous populations (representing almost the entire native distribution area) and eight non‐indigenous (cultivated or naturalized) populations were analyzed. Their essential‐oil yield ranged from 0.25 to 3.48%. Within the total of 80 detected compounds, ten (β‐pinene, 1,8‐cineole, cis‐thujone, trans‐thujone, camphor, borneol, trans‐caryophyllene, α‐humulene, viridiflorol, and manool) represented 42.60 to 85.70% of the components in the analyzed essential oils. Strong positive correlations were observed between the contents of trans‐caryophyllene and α‐humulene, α‐humulene and viridiflorol, and viridiflorol and manool. Principal component analysis (PCA) on the basis of the contents of the ten main compounds showed that four principal components had an eigenvalue greater than 1 and explained 79.87% of the total variation. Performing cluster analysis (CA), the sage populations could be grouped into four distinct chemotypes (A–D). The essential oils of 14 out of the 25 populations of Dalmatian sage belonged to Chemotype A and were rich in cis‐thujone and camphor, with low contents of trans‐thujone. The correlation between the essential‐oil composition and geographic variables of the indigenous populations was not significant; hence, the similarities in the essential‐oil profile among populations could not be explained by the physical proximity of the populations. Additionally, the southeastern populations tended to have higher EO yields than the northwestern ones.     

Phytochemical Fingerprints of Copaiba Oils (Copaifera multijuga Hayne) Determined by Multivariate Analysis

Oils of various species of Copaifera are commonly found in pharmacies and on popular markets and are widely sold for their medicinal properties. However, the chemical variability between and within species and the lack of standardization of these oils have presented barriers to their wider commercialization. With the aim to recognize patterns for the chemical composition of copaiba oils, 22 oil samples of C. multijuga Hayne species were collected, esterified with CH₂N₂, and characterized by GC‐FID and GC/MS analyses. The chromatographic data were processed using hierarchical cluster analysis (HCA) and principal component analysis (PCA). In total, 35 components were identified in the oils, and the multivariate analyses (MVA) allowed the samples to be divided into three groups, with the sesquiterpenes β‐caryophyllene and caryophyllene oxide as the main components. These sesquiterpenes, which were detected in all the samples analyzed in different concentrations, were the most important constituents in the differentiation of the groups. There was a prevalence of sesquiterpenes in all the oils studied. In conclusion, GC‐FID and GC/MS analyses combined with MVA can be used to determine the chemical composition and to recognize chemical patterns of copaiba oils.     

Variability of the Needle Essential Oils of Juniperus deltoides R.P.Adams from Different Populations in Serbia and Croatia

The essential‐oil compositions of one Croatian and three Serbian populations of Juniperus deltoides R.P.Adams have been determined by GC/MS analysis. In total, 147 compounds were identified, representing 97.3–98.3% of the oil composition. The oils were dominated by monoterpenes, which are characteristic components for the species of the section Juniperus. Two monoterpenes, α‐pinene and limonene, were the dominant constituents, with a summed‐up average content of 49.45%. Statistical methods were used to determine the diversity of the terpene classes and the common terpenes between the newly described J. deltoides populations from Serbia and Croatia. Only reports on several specimens from this species have been reported so far, and there are no studies that treat population diversity. Cluster analysis of the oil contents of 21 terpenes showed high correlation with the geographical distribution of the populations, separating the Croatian from the Serbian populations. The comparison of the essential‐oil compositions obtained in the present study with literature data, showed the separation of J. deltoides and J. oxycedrus ssp. oxycedrus from the western Mediterranean region.     

Bark Essential Oil of Cedrelopsis grevei from Madagascar: Investigation of Steam‐Distillation Conditions

The effect of the distillation time on the yield and chemical composition of the bark essential oil of Cedrelopsis grevei Baill. was investigated. Distillation kinetics were determined for three batches of bark sampled from two sites, i.e., Itampolo (batches IT1 and IT2) and Salary (SAL), located in a region in the south of Madagascar with characteristically large populations of C. grevei. The bark samples were subjected to steam distillation, and the essential oil was collected at 3‐h intervals. The total yield (calculated after 14 h of distillation) varied from 0.9 to 1.7%, according to the batch tested. Moreover, the essential oils obtained were characterized by GC‐FID and GC/MS analyses. During the course of the distillation, the relative percentages of the most volatile components (monoterpenes and sesquiterpene hydrocarbons) diminished progressively, whereas the least volatile ones (oxygenated derivatives) increased at a consistent rate. Principal component analysis (PCA) and agglomerative hierarchical clustering analysis (AHC) of the results, performed on 13 principal components, allowed distinguishing three chemical groups, corresponding to the three batches, irrespective of the distillation time. This indicated that the chemical variability currently observed with commercial samples is not mainly linked to the experimental conditions of the extraction process, as the distillation time did not significantly alter the chemical composition of the essential oils.     

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.     

Variation in Volatile Leaf Oils of 13 Eucalyptus Species Harvested from Souinet Arboreta (Tunisia)

Hydrodistillation of the dried leaves of 13 species of the genus Eucalyptus L' Hér ., viz., E. bicostata Maiden, Blakely & Simmonds , E. cinerea F. Muell . ex Benth ., E. exerta F. Muell ., E. gigantea Hook . f ., E. gunnii Hook . f ., E. macarthurii Deane & Maiden ., E. macrorrhyncha F. Muell ., E. maidenii F. Muell ., E. odorata Behr ., E. pauciflora Sieber ex Sprengel , E. sideroxylon A. Cunn . ex Woolls , E. tereticornis Sm ., and E. viminalis Labill ., harvested from Souinet arboreta (region of Ain Draaham, north of Tunisia) in June 2006, afforded essential oils in yields varying from 0.5±0.2 to 3.9±0.4%, dependent on the species. E. cinerea and E. exerta provided the highest and the lowest percentage of essential oil amongst all the species examined, respectively. Analysis by GC (RI) and GC/MS allowed the identification of 142 components, representing 81.5 to 98.9% of the total oil. The contents of the different samples varied according to the species. The main components were 1,8‐cineole ( 1 ), followed by cryptone, spathulenol ( 4 ), p‐cymene ( 2 ), viridiflorol ( 6 ), globulol ( 7 ), β‐eudesmol, α‐terpineol ( 5 ), limonene ( 8 ), D ‐piperitone, α‐pinene ( 3 ), cuminal, and γ‐eudesmol. The principal component and the hierarchical cluster analyses separated the 13 Eucalyptus leaf essential oils into three groups, each constituting a chemotype.     

Variation in Volatile Leaf Oils of Eleven Eucalyptus Species Harvested from Korbous Arboreta (Tunisia)

Hydrodistillation of the dried leaves of eleven species of the genus Eucalyptus L 'Hér ., i.e., E. astringens Maiden , E. camaldulensis Dehnh ., E. diversifolia Bonpl ., E. falcata Turcz ., E. ficifolia F. Muell ., E. gomphocephala DC., E. lehmannii (Schauer ) Benth ., E. maculata Hook ., E. platypus Hook ., E. polyanthemos Schauer, and E. rudis Endl ., harvested from Korbous arboreta (region of Nabeul, northeast of Tunisia) in April 2006, afforded essential oils in yields varying from 0.1±0.1 to 3.8±0.1%, dependent on the species. E. astringens and E. ficifolia showed the highest and the lowest mean percentage of essential oil amongst all the species examined, respectively. Analysis by GC (RI) and GC/MS allowed the identification of 138 components, representing 74.0 to 99.1% of the total oil. The contents of the different samples varied according to the species. The main components were 1,8‐cineole, followed by trans‐pinocarveol ( 1 ), spathulenol ( 2 ), α‐pinene, p‐cymene, (E,E)‐farnesol, cryptone, globulol ( 3 ), β‐phellandrene, α‐terpineol, viridiflorol, and α‐eudesmol. The principal‐component and the hierarchical‐cluster analyses separated the eleven Eucalyptus leaf essential oils into seven groups, each constituting a chemotype.     

Variation in Volatile Leaf Oils of Twelve Eucalyptus Species Harvested from Hajeb Layoun Arboreta (Tunisia)

Hydrodistillation of the dried leaves of twelve species of the genus Eucalyptus L' Hér ., i.e., E. brockwayi C. A. Gardn ., E. gracilis F. Muell ., E. gillii Maiden , E. largiflorens F. Muell ., E. loxophleba Benth ., E. occidentalis Endl ., E. oldfieldii F. Muell ., E. salmonophloia F. Muell ., E. sargentii Maiden , E. stricklandii Maiden , E. torquata Luehm ., and E. woodwardii Maiden , harvested from Hajeb Layoun arboreta (region of Kairouan, central Tunisia) in January 2005, afforded essential oils in yields varying from 0.5±0.1 to 5.7±0.5%, dependent on the species. E. sargentii and E. brockwayi provided the highest and the lowest percentage of essential oil amongst all the species examined, respectively. Analysis by GC (RI) and GC/MS allowed the identification of 133 components, representing 92.9–98.8% of the total oil. The contents of the different samples varied according to the species. The main components were 1,8‐cineole, terpinen‐4‐ol, α‐pinene ( 2 ), p‐cymene, aromadendrene ( 1 ), globulol ( 5 ), trans‐pinocarveol ( 6 ), spathulenol ( 7 ), β‐eudesmol, torquatone ( 3 ), and 4‐methylpentan‐2‐yl acetate ( 8 ). The principal component analysis and the hierarchical clustering indicated that the volatile leaf oil composition of the twelve Eucalyptus species could be clearly differentiated.     

Essential‐Oil Composition of Daucus carota ssp. major (Pastinocello Carrot) and Nine Different Commercial Varieties of Daucus carota ssp. sativus Fruits

The chemical composition of the essential oils obtained by hydrodistillation from the pastinocello carrot, Daucus carota ssp. major (Vis.) Arcang . (flowers and achenes), and from nine different commercial varieties of D. carota L. ssp. sativus (achenes) was investigated by GC/MS analyses. Selective breeding over centuries of a naturally occurring subspecies of the wild carrot, D. carota L. ssp. sativus, has produced the common garden vegetable with reduced bitterness, increased sweetness, and minimized woody core. On the other hand, the cultivation of the pastinocello carrot has been abandoned, even if, recently, there has been renewed interest in the development of this species, which risks genetic erosion. The cultivated carrot (D. carota ssp. sativus) and the pastinocello carrot (D. carota ssp. major) were classified as different subspecies of the same species. This close relationship between the two subspecies urged us to compare the chemical composition of their essential oils, to evaluate the differences. The main essential‐oil constituents isolated from the pastinocello fruits were geranyl acetate (34.2%), α‐pinene (12.9%), geraniol (6.9%), myrcene (4.7%), epi‐α‐bisabolol (4.5%), sabinene (3.3%), and limonene (3.0%). The fruit essential oils of the nine commercial varieties of D. carota ssp. sativus were very different from that of pastinocello, as also confirmed by multivariate statistical analyses.     

Chemical Composition and Phytotoxic Effects of Essential Oils Obtained from Ailanthus altissima (Mill.) Swingle Cultivated in Tunisia

Ailanthus altissima Mill. Swingle (Simaroubaceae), also known as tree of heaven, is used in the Chinese traditional medicine as a bitter aromatic drug for the treatment of colds and gastric diseases. In Tunisia, Ailanthus altissima is an exotic tree, which was introduced many years ago and used particularly as a street ornamental tree. Here, the essential oils of different plant parts of this tree, viz., roots, stems, leaves, flowers, and samaras (ripe fruits), were obtained by hydrodistillation. In total, 69 compounds, representing 91.0–97.2% of the whole oil composition, were identified in these oils by GC‐FID and GC/MS analyses. The root essential oil was clearly distinguishable for its high content in aldehydes (hexadecanal ( 1 ); 22.6%), while those obtained from flowers and leaves were dominated by oxygenated sesquiterpenes (74.8 and 42.1%, resp.), with caryophyllene oxide ( 4 ) as the major component (42.5 and 22.7%, resp.). The samara oil was rich in the apocarotenoid derivative hexahydrofarnesyl acetone ( 6 ; 58.0%), and the oil obtained from stems was characterized by sesquiterpene hydrocarbons (54.1%), mainly β‐caryophyllene (18.9%). Principal component and hierarchical cluster analyses separated the five essential oils into four groups, each characterized by the major oil constituents. Contact tests showed that the germination of lettuce seeds was totally inhibited by all the essential oils except of the samara oil at a dose of 1 mg/ml. The flower oil also showed a significant phytotoxic effect against lettuce germination at 0.04 and 0.4 mg/ml (?55.0±3.5 and ?85.0±0.7%, resp.). Moreover, the root and shoot elongation was even more affected by the oils than germination. The inhibitory effect of the shoot and root elongation varied from ?9.8 to ?100% and from ?38.6 to ?100%, respectively. Total inhibition of the elongation (?100%) at 1 mg/ml was detected for all the oils, with the exception of the samara oil (?74.7 and ?75.1% for roots and shoots, resp.).     

Essential‐Oil Diversity of Three Calamintha Species from Greece

The aim of the present study was to contribute to the knowledge of the essential‐oil composition of the Calamintha officinalis‐nepeta complex in Greece and to clarify the main patterns of its variation. The oils obtained from 22 wild‐growing populations of C. glandulosa, C. nepeta, and C. menthifolia were studied. They could be classified into two different chemotypes, which correspond to the main biosynthetic routes of the C(3)‐oxygenated p‐menthane compounds. Chemotype I includes oils rich in trans‐piperitone oxide, cis‐piperitone oxide, and piperitenone oxide, while Chemotype II comprises oils rich in pulegone and menthone or menthone and isomenthone. Within both chemotypes, quantitative fluctuations of the main components were observed. Comparison with published data showed that the presence of Chemotype II has not been observed before in C. menthifolia, while Chemotype I has been reported in C. nepeta plants from Greece for the first time.     

Volatile Compounds in Thymus sect. Teucrioides (Lamiaceae): Intraspecific and Interspecific Diversity,Chemotaxonomic Significance and Exploitation Potential

Thymus sect. Teucrioides comprises three species, namely, T. hartvigii, T. leucospermus, and T. teucrioides, distributed in Greece and Albania. The volatile constituents of all species of the section were obtained by hydrodistillation and investigated by GC‐FID and GC/MS analyses. Twenty populations were sampled and a total of 103 compounds were identified, representing 98.0–99.9% of the oil compositions. The oils were mainly characterized by high contents of monoterpene hydrocarbons (42.7–92.4%), with the exception of three oils for which oxygenated monoterpenes were the dominating constituents, viz., that of T. hartvigii ssp. macrocalyx, with linalool as main compound (89.2±0.5%), and those of T. hartvigii ssp. hartvigii and of one population of T. teucrioides ssp. candilicus, containing thymol as major component (46.4±3.1 and 38.2±3.9%, resp.). The most common compound in the oils of the 20 populations of the section was p‐cymene. Considerable variation was detected within and among populations, and seven chemotypes were distinguished, i.e., p‐cymene, linalool, p‐cymene/thymol, p‐cymene/γ‐terpinene, p‐cymene/borneol, p‐cymene/γ‐terpinene/borneol, and p‐cymene/linalool chemotypes. Different chemotypes may exist in the same population. Multivariate statistical analyses enabled the segregation of the oils within Thymus sect. Teucrioides into two groups, one consisting of the three subspecies of T. teucrioides and the second comprising the species T. hartvigii and T. leucospermus. A linalool‐rich chemotype, unique within the section, distinguished the oil of T. hartvigii ssp. macrocalyx from all other oils. The high oil content of p‐cymene and the preference for serpentine substrates render T. teucrioides species promising for future exploitation.     

Essential‐Oil Composition of the Fruits of Six Heracleum L. Species from Iran: Chemotaxonomic Significance

The fruit essential oils of Heracleum persicum, H. rechingeri, H. gorganicum, H. rawianum, H. pastinacifolium, and H. anisactis from Iran were obtained by hydrodistillation and characterized by GC‐FID and GC/MS analyses. The oils of the six species were compared to determine the similarities and differences among their compositions. Overall, 36 compounds were identified in the fruit oils, accounting for 92.40–96.74% of the total oil compositions. Aliphatic esters constituted the main fraction of the oils (86.61–94.31%), with octyl acetate and hexyl butyrate as the major components. The oil compositions of species belonging to section Pubescentia (H. persicum, H. gorganicum, and H. rechingeri) were discriminated by equally high contents of both octyl acetate (13.84–20.48%) and hexyl butyrate (17.73–38.36%). On the other hand, the oils of H. rawianum, H. pastinacifolium and H. anisactis, belonging to section Wendia, showed lower hexyl butyrate contents (3.62–6.6%) and higher octyl acetate contents (48.71–75.36%) than the former. Moreover, isoelemicin was identified at low amounts (0.10–2.51%) only in the oils of the latter species. The differences in the oil composition among the six species were investigated by hierarchical cluster and principal component analyses, which indicated that the oil composition confirmed well the taxonomical classification based on the morphological and botanical data, and, thus, may provide a reliable marker to discriminate Heracleum species at the intersectional level.     

Chemodiversity of Volatile Oils in Thapsia garganica L. (Apiaceae)

The chemical composition of the volatile oils obtained from the roots, leaves, flowers, and stems of Thapsia garganica of Tunisian origin was investigated by GC‐FID and GC/MS analyses. Sesquiterpene hydrocarbons and oxygenated monoterpenes were predominant in the oils of all plant parts. Bicyclogermacrene (21.59–35.09%) was the main component in the former compound class, whereas geranial (3.31–14.84%) and linalool (0.81–10.9%) were the most prominent ones in the latter compound class. Principal‐component (PCA) and hierarchical‐cluster (HCA) analyses revealed some common constituents, but also significant variability amongst the oils of the different plant parts. This organ‐specific oil composition was discussed in relation to their biological and ecological functions. For the evaluation of the intraspecific chemical variability in T. garganica, the composition of the flower volatile oils from four wild populations was investigated. Bicyclogermacrene, linalool, and geranial were predominant in the oils of three populations, whereas epicubenol, β‐sesquiphellandrene, and cadina‐1,4‐diene were the most prominent components of the oil of one population. PCA and HCA allowed the separation of the flower oils into three distinct groups, however, no relationship was found between the volatile‐oil composition and the geographical distribution and pedoclimatic conditions of the studied populations.     

Chemical Composition and Allelopathic Potential of Essential Oils Obtained from Acacia cyanophylla Lindl. Cultivated in Tunisia

Acacia cyanophylla Lindl . (Fabaceae), synonym Acacia saligna (Labill .) H. L.Wendl ., native to West Australia and naturalized in North Africa and South Europe, was introduced in Tunisia for rangeland rehabilitation, particularly in the semiarid zones. In addition, this evergreen tree represents a potential forage resource, particularly during periods of drought. A. cyanophylla is abundant in Tunisia and some other Mediterranean countries. The chemical composition of the essential oils obtained by hydrodistillation from different plant parts, viz., roots, stems, phyllodes, flowers, and pods (fully mature fruits without seeds), was characterized for the first time here. According to GC‐FID and GC/MS analyses, the principal compound in the phyllode and flower oils was dodecanoic acid ( 4 ), representing 22.8 and 66.5% of the total oil, respectively. Phenylethyl salicylate ( 8 ; 34.9%), heptyl valerate ( 3 ; 17.3%), and nonadecane (36%) were the main compounds in the root, stem, and pod oils, respectively. The phyllode and flower oils were very similar, containing almost the same compounds. Nevertheless, the phyllode oil differed from the flower oil for its higher contents of hexahydrofarnesyl acetone ( 6 ), linalool ( 1 ), pentadecanal, α‐terpineol, and benzyl benzoate ( 5 ) and its lower content of 4 . Principal component and hierarchical cluster analyses separated the five essential oils into four groups, each characterized by its main constituents. Furthermore, the allelopathic activity of each oil was evaluated using lettuce (Lactuca sativa L.) as a plant model. The phyllode, flower, and pod oils exhibited a strong allelopathic activity against lettuce.     

Variation in volatile leaf oils of five Eucalyptus species harvested from Jbel Abderrahman arboreta (Tunisia)

Hydrodistillation of the dried leaves of five species of the genus Eucalyptus L' Hér ., viz., E. dundasii Maiden , E. globulus Labill ., E. kitsoniana Maiden , E. leucoxylon F. Muell ., and E. populifolia Hook ., harvested from Jbel Abderrahman arboreta (region of Nabeul, northeast of Tunisia) in April 2006, afforded essential oils in yields varying from 0.9±0.3 to 3.8±0.6%, dependent on the species. E. globulus and E. Kitsoniana provided the highest and the lowest percentage of essential oil amongst the species examined, respectively. Analysis by GC (RI) and GC/MS allowed the identification of 127 compounds, representing 93.8 to 98.7% of the total oil composition. The contents of the different samples varied according to the species. The main components were 1,8‐cineole ( 2 ; 4.7–59.2%), followed by α‐pinene ( 1 ; 1.9–23.6%), trans‐pinocarveol ( 6 ; 3.5–21.6%), globulol ( 8 ; 4.3–12.8%), p‐cymene ( 3 ; 0.5–6.7%), α‐terpineol (1.5–4.5%), borneol (0.2–4.4%), pinocarvone (1.1–3.8%), aromadendrene (1.4–3.4%), isospathulenol (0.0–1.9%), fenchol ( 4 ; 0.1–2.5%), limonene (1.0–2.4%), epiglobulol (0.6–2.1%), viridiflorol ( 9 ; 0.8–1.8%), and spathulenol (0.1–1.6%). E. leucoxylon was the richest species in 2 . Principal component analysis (PCA) and hierarchical cluster analysis (HCA) separated the five Eucalyptus leaf essential oils into four groups, each constituting a chemotype.     

Variation in volatile leaf oils of seven eucalyptus species harvested from Zerniza arboreta (Tunisia)

Leaves of seven species of the genus Eucalyptus L'Hér., viz., E. cladocalyx F. Muell., E. citriodora Hook., E. diversicolor F. Muell., E. fasciculosa F. Muell., E. grandis W. Hill, E. ovata Labill., and E. botryoides Sm., were harvested from Zerniza arboreta (region of Sejnene, northwest of Tunisia) in June 2007. Of the latter species, leaves were collected from trees having two origins, Morocco and Italy. Hydrodistillation of the dried leaves provided essential oils in yields varying from 0.4±0.0 to 3.3±0.1%, according to the species. E. citriodora had the highest mean percentage of essential oil amongst the species examined, whereas the lowest one was obtained for E. botryoides originating from Morocco. Analysis by GC (RI) and GC/MS allowed the identification of 140 compounds, representing 92.5 to 99.4% of the total oil composition. The contents of the different samples varied according to the species. The main components were 1,8-cineole (2), followed by α-pinene (1), p-cymene, borneol, α-terpineol, cryptone, spathulenol, trans-pinocarveol (4), bicyclogermacrene (5), caryophyllene oxide, and β-phellandrene. Principal components analysis and hierarchical cluster analysis separated the eight Eucalyptus leaf essential oils into five groups, each constituting a chemotype.     

Composition of n‐Alkanes in Natural Populations of Pinus nigra from Serbia – Chemotaxonomic Implications

This is the first report on the composition and variability of the needle‐wax n‐alkanes in natural populations of Pinus nigra in Serbia. Samples of 195 trees from seven populations belonging to several infraspecific taxa (ssp. nigra, var. gocensis, ssp. pallasiana, and var. banatica) were analyzed. In general, the size of the n‐alkanes ranged from C₁₆ to C₃₃, with the exception of ssp. nigra, for which it ranged from C₁₈ to C₃₃. The most abundant were C₂₃‐, C₂₅‐, C₂₇‐, and C₂₉‐alkanes. The needle waxes of Populations I–III and V were characterized by a higher content of C₂₃‐, C₂₅‐, and C₂₇‐alkanes and a lower content of C₂₄‐, C₂₆‐, C₂₈‐, and C₃₀‐alkanes, compared to the other populations, and the trees of these populations could be assigned to ssp. nigra. The samples of Population VI were characterized by higher amounts of C₂₂‐, C₂₄‐, C₃₀‐, and C₃₂‐alkanes and lower amounts of C₂₅‐ and C₂₇‐alkanes, and the trees could be considered as ssp. pallasiana. The samples of Population VII, consisting of trees belonging to var. banatica, were richer in C₂₉‐, C₃₁‐, and C₃₃‐alkanes. The wax compositions of Populations IV and V, both composed of trees previously determined as P. nigra var. gocensis, showed a tendency of splitting. Indeed, the alkane composition of Population IV was closer to that of ssp. pallasiana pines, while that of Population V was more similar to that of ssp. nigra pines. From the results presented here, it is obvious that in the central part of the Balkan Peninsula, significant diversification and differentiation of the populations of black pine exists, and these populations could be defined as different intraspecific taxa. Our results also indicate the validity of n‐alkanes as chemotaxonomic characters within this aggregate.