The determination of n-alkanes in the cuticular wax of leaves of Ludwigia adscendens L

An n-hexane extract of fresh, mature leaves of Ludwigia adscendens, containing a thin layer of epicuticular waxes, has been analysed for the first time by TLC, IR and GC using standard hydrocarbons. The leaves contained 22 identified long chain (C15-C36) n-alkanes, accounting for 74.27% of the hydrocarbons present, and an unknown number of unidentified branched chain alkanes. The predominant n-alkane was C25 (11.02%), whilst C18 (7.62%), C20 (6.14%), C29 (5.36%) and C27 (5.29%) n-alkanes were moderately abundant: the C35 homologue was present only in minor amounts (0.22%).     

Essential oils from the leaves of three New Zealand species of Pseudopanax (Araliaceae)

Essential oils from three of the eleven endemic New Zealand species of Pseudopanax, P. arboreus, P. discolor and P. lessonii, were found to have a fairly uniform composition which was different from that of the oils of Raukaua species that were formerly classified in the Pseudopanax genus. Oils of the three Pseudopanax species all contained significant proportions of viridiflorol and a closely related unidentified hydroazulene alcohol in common. In addition, the oil of P. arboreus contained bicyclogermacrene, linalool and long chain hydrocarbons. The oil of P. discolor contained nerolidol in abundance (36.3%) together with linalool and epi-alpha-muurolol. The oil of P. lessonii contained a complex mixture of sesquiterpene alcohols including epi-alpha-muurolol and a mixture of long chain hydrocarbons. Nerolidol and linalool provided the oil of P. discolor with a pleasant floral aroma, but the yield of oil was very low (0.01%).     

Salvia verbenaca L. essential oil: Variation of yield and composition according to collection site and phenophase

The effect of the collection sites and phenophase on yield and chemical composition of Salvia verbenaca essential oils was evaluated. The essential oil constituents were assessed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). The highest essential oil yields were observed for samples of the higher semi-arid bioclimate and at the flowering period. Eighty-five volatile constituents were identified and their percentages varied significantly (p < 0.05) depending on the collection site and the phenological stage. According to the plants origin, essential oils were dominated by monoterpene hydrocarbons, oxygenated monoterpenes and sesquiterpene hydrocarbons. The monoterpene hydrocarbons (31.9%) predominate at the flowering stage whereas oxygenated sesquiterpenes (27.5%) at the early fruiting stage. The sesquiterpene hydrocarbons (28.2%) was the most represented chemical class at late fruiting. On the basis of GC-MS data, the major identified volatile constituents were viridiflorol (3.4–17.7%), α-pinene (0.7–15.9%), β-caryophyllene (1.0–15.3%) and p-cymene (1.3–14.2%). S. verbenaca contains a diversity of bioactive constituents which shows large variations as affected by the collection sites and phenophase.     

Terpenes from the essential oil of Cymbopogon distans

A GC/MS study of the hydrocarbon fraction and the fraction containing oxygenated compounds showed the presence of 12 monoterpene hydrocarbons (28.4%), 13 sesquiterpene hydrocarbons (32.8%), 3 sesquiterpene alcohols (27.2%), 2 esters (7.2%) and 3 carbonyl compounds (4.4%) in the essential oil of Cymbopogon distans. Of these, 27 compounds have been identified.     

epi-Cubebanes from Solidago canadensis

GC-MS of the essential oil prepared by hydrodistillation of the green parts of a specimen of Solidago canadensis collected near Katowice, Poland, revealed two new sesquiterpene hydrocarbons. Their EI mass spectra resembled the mass spectrum of beta-ylangene (1) but the retention indices of the new compounds differed markedly from this known compound. After isolation of the new compounds by preparative GC their investigation by one- and two-dimensional NMR techniques resulted in the identification of 6-epi-alpha-cubebene (2) (minor constituent, 1.5%) and 6-epi-beta-cubebene (3) (major constituent, 20.5%).     

Volatile flavor components of ripe and overripe ki-mikans (Citrus flaviculpus Hort. ex Tanaka) in comparison with Hyuganatsu (Citrus tamurana Hort. ex Tanaka)

The volatile flavor components of ripe and overripe ki-mikan (Citrus flaviculpus Hort. ex Tanaka) peel oil samples, which had been isolated by cold-pressing, were investigated by capillary GC and GC-MS, and compared with the Hyuganatsu (Citrus tamurana Hort. ex Tanaka) flavor. Limonene (ripe fruit, 82.44%; overripe fruit, 73.10%) was the most abundant compound in the ki-mikan oil, this being followed by gamma-terpinene (8.83% and 13.74%), trans-beta-farnesene (1.76% and 3.12%) and myrcene (1.54% and 1.13%). The composition of overripe ki-mikan oil was characterized by higher amounts of aliphatic and sesquiterpene hydrocarbons, monoterpene and sesquiterpene alcohols, ketones and esters than that of ripe ki-mikan oil. Monoterpene hydrocarbons, especially limonene (84.78%), were predominant in Hyuganatsu oil. The CPO composition of ki-mikan was qualitatively similar to that of Hyuganatsu, but differed quantitatively. The content of sesquiterpene hydrocarbons was higher in the ki-mikan oil samples than in Hyuganatsu oil, while ketones showed the opposite predominance. These differences were more evident in the trans-beta-farnesene and l-carvone contents. The ratio of both these compounds could be used to distinguish ki-mikan oil from Hyuganatsu oil.     

Essential‐Oil Variability in Natural Populations of Pinus mugo Turra from the Julian Alps

The composition and variability of the terpenes and their derivatives isolated from the needles of a representative pool of 114 adult trees originating from four natural populations of dwarf mountain pine (Pinus mugo Turra ) from the Julian Alps were investigated by GC‐FID and GC/MS analyses. In total, 54 of the 57 detected essential‐oil components were identified. Among the different compound classes present in the essential oils, the chief constituents belonged to the monoterpenes, comprising an average content of 79.67% of the total oil composition (74.80% of monoterpene hydrocarbons and 4.87% of oxygenated monoterpenes). Sesquiterpenes were present in smaller amounts (average content of 19.02%), out of which 16.39% were sesquiterpene hydrocarbons and 2.62% oxygenated sesquiterpenes. The most abundant components in the needle essential oils were the monoterpenes δ‐car‐3‐ene, β‐phellandrene, α‐pinene, β‐myrcene, and β‐pinene and the sesquiterpene β‐caryophyllene. From the total data set of 57 detected compounds, 40 were selected for principal‐component analysis (PCA), discriminant analysis (DA), and cluster analysis (CA). The overlap tendency of the four populations suggested by PCA, was as well observed by DA. CA also demonstrated similarity among the populations, which was the highest between Populations I and II.     

Sesquiterpene constituents from the essential oil of the liverwort Plagiochila asplenioides

The essential oil of the liverwort Plagiochila asplenioides from two different locations in Northern Germany were investigated by chromatographic and spectroscopic methods. Seven compounds were isolated by preparative gas chromatography (GC) and their structures investigated by mass spectrometry (MS), NMR techniques and chemical correlations in combination with enantioselective GC. In addition to known constituents, aromadendra-1(10),3-diene, two aromatic sesquiterpene hydrocarbons, bisabola-1,3,5,7(14)-tetraene and bisabola-1,3,5,7-tetraene, three sesquiterpene ethers, muurolan-4,7-peroxide, plagiochilines W and X, in addition to ent-4-epi-maaliol, could be identified as natural compounds for the first time.     

Essential oil composition of Eryngium rosulatum P.W. Michael ined.: A new undescribed species from eastern Australia

The essential oil composition from the aerial parts of a new Eryngium species from Australia, Eryngium rosulatum P.W. Michael ined., has been analysed by GC and GC/MS. A total of 34 compounds have been identified representing around 80% of the total oil. The main constituents of the oil were found to be β-elemene (16.0%) and bicyclogermacrene (12.5%). Other representative compounds were identified as δ-elemene (7.0%) and (E)-caryophyllene (5.9%). The sesquiterpene fraction (75.0%) was predominant in the essential oil of this species, most of these were hydrocarbons (53.8%). This paper represents the first study on this new, undescribed Australian species and its chemical composition.     

Composition of the essential oil from cell suspension cultures of Achillea millefolium ssp. millefolium

The composition of the essential oil isolated from Achillea millefolium L. ssp. millefolium cell suspension cultures was analysed by GC and GC-MS. The yield of the oil obtained by hydrodistillation or a simultaneous distillation -extraction of these cultures, harvested at days 8–10 (end of exponential phase), was 0.001 % (w/w). The analysis of the volatiles showed the presence of thirteen components; monoterpenes amounted to 5%, sesquiterpene hydrocarbons attained 40%, while eugenol, demethoxyencecalin and two unidentified compounds amounted to 45% of the total oil. Several methods were tested in an attempt to increase the essential oil production by the cultures: growth on solid medium, growth in light, use of a different culture medium, elicitation with cellulase or yeast extract, and growth in a two-phase system. Of the different methods tested, the growth in B5⁺ medium with Miglyol 812 led to the highest essential oil yield (0.002%, w/w), and resulted in a more diverse oil composition.     

Chemical Composition of Essential Oils and Aromatic Waters from Different Italian Anthemis maritima Populations

The chemical composition of the essential oils and aromatic waters isolated from six Italian Anthemis maritima populations was determined by GC‐FID and GC/MS analyses. In total, 122 and 100 chemical compounds were identified in the essential oils and the aromatic waters, respectively. The main compound classes represented in the oils were monoterpene hydrocarbons, oxygenated monoterpenes, sesquiterpene hydrocarbons, oxygenated sesquiterpenes, and terpene esters. Multivariate chemometric techniques such as cluster analysis (CA) and principal coordinate analysis (PCO) were used to classify the samples according to the geographical origin. Statistical analysis allowed the attribution of the analyzed populations to different chemotype groups.     

Assimilation of Hydrocarbons by Pseudomonas Strains Isolated from Human Clinical Specimens

Twenty strains of Pseudomonas isolated from human clinical specimens on routine laboratory media, without hydrocarbon enrichment and unselected for their growth on hydrocarbons, were tested for their ability to utilize a series of eight n-alkanes and two 1-alkenes as a sole carbon and energy source for growth. Hydrocarbon assimilation does occur with such isolates relative to the chain length and the degree of saturation of the hydrocarbon. The data presented show that all 16 stains of Pseudomonas aeruginosa studied grew readily on dodecane through hexadecane and on 1-hexadecene. In addition, most strains of this species grew on undecane and 1-dodecene after prolonged incubation. There was a long lag period, usually a minimum of 4 days, before onset of growth on any hydrocarbon. In no case did hexane or decane support growth. Two strains each of P. maltophilia and P. stutzeri were unable to grow on any of the hydrocarbons tested. Hexane in concentrations above 1% (vol/vol) is bactericidal toward the Pseudomonas inoculum. It is toxic even to cells utilizing different hydrocarbon for growth. The addition of 1% hexane to 1% (vol/vol) hexadecane markedly prolonged the lag phase of P. aeruginosa utilizing the hexadecane for growth.     

Application of multidimensional gas chromatography to the enantioselective characterisation of the essential oil of Eupatorium buniifolium Hooker et Arnott

The qualitative and quantitative composition of the essential oil from aerial parts of Eupatorium buniifolium Hooker et Arnott (Asteraceae) has been investigated for the first time. The essential oils were obtained by steam distillation of leaves and analysed by GC-MS; 44 components were identified. Monoterpene and sesquiterpene hydrocarbons, especially alpha-pinene (14.7%), beta-elemene (12.2%), germacrene D (11.5%), trans-beta-guaiene (6.5%) and (E)-caryophyllene (4.3%), were the major constituents found in the oils. The characterisation of E. buniifolium by enantioselective GC was performed by evaluation of the enantiomeric ratios of alpha-pinene, sabinene, beta-pinene, limonene, terpinen-4-ol and germacrene D.     

Analysis of the volatile essential oils of Murraya koenigii and Pandanus latifolius

Using well-established techniques, samples were obtained of the volatile essential oils of the two types of curry leaf, Murraya koenigii and Pandanus latifolius. Both contained mainly terpenes, and M. koenigii produced less than 4% of other components with eight monoterpene hydrocarbons (ca 16%) and 17 sesquiterpene hydrocarbons (ca 80%) being obtained. The most important constituents of M. koenigii are β-caryophyllene, β-gurjunene, β-elemene, β-phellandrene and β-thujene. The volatile essential oil of P. latifolius also contained mainly sesquiterpene hydrocarbons (6–42%) but the only monoterpene was linalool (ca 6%). Nearly 2000 times the total quantity of aroma volatiles was produced by M. koenigii compared with P. latifolius, and this partly explains the observed stronger flavour potency of the former.     

Seasonal variation of the chemical constituents of the essential oil of Santolina etrusca from Italy

The seasonal variation of the essential oil, in terms of both yield and composition, of a population of Santolina etrusca (Asteraceae) is reported in detail for different aerial parts, including sterile branches, fertile branches, and capitula. The yields generally increased from November to June, and then decreased in August and September. The main constituents of the sterile branches were 1,8-cineole and viridiflorol. The oil from fertile branches was characterized by myrcene as principal compound, whereas the essential oil obtained from the capitula contained germacrene D as the main constituent. Several compounds, as identified by GC and GC/MS, were found to prevail during the cold season.     

Chemical study of the essential oil of Cyperus rotundus.

Minor constituents of the essential oil of Cyperus rotundus have been investigated. The three new sesquiterpene hydrocarbons (-)-isorotundene, (-)-cypera-2,4(15)-diene, (-)-norrotundene and the ketone (+)-cyperadione were isolated and their structures elucidated. The absolute configuration of (-)-rotundene was derived by chemical correlation and enantioselective gas chromatography.     

Sesquiterpene constituents in Petasites hybridus

The essential oil of the rhizomes of Petasites hybridus (Asteraceae) was investigated by gas chromatography, mass spectrometry, 1- and 2-dimensional NMR techniques and chemical correlations. Two new sesquiterpene hydrocarbons, petasitene and pethybrene, could be identified. Petasitene is the parent sesquiterpene hydrocarbon to the known norsesquiterpene albene. The absolute configuration of petasitene could be assigned by conversion of natural albene to petasitene by partial synthesis. Pethybrene is a tricyclic sesquiterpene hydrocarbon, which rearranges to the structurally related alpha-isocomene under acidic conditions. Several sesquiterpenes were isolated from the hydrodistillation products of Petasites hybridus and investigated by spectroscopic methods and chemical correlations     

Chemical Composition and Biological Activities of Tunisian Cupressus arizonica Greene Essential Oils

The chemical composition of the essential oils obtained by hydrodistillation of leaves, stems, and female cones of Cupressus arizonica Greene , grown in Tunisia, was studied by GC‐FID and GC/MS analyses. Altogether, 62 compounds were identified, 62 in the leaf oil, 19 in the cone oil, and 24 in the stem oil. The cone and stem oils were mainly composed by monoterpene hydrocarbons (96.6 and 85.2%, resp.). In the leaf oil, the total sesquiterpene fraction constituted 36.1% and that of the monoterpene hydrocarbons 33.8% of the total oil composition. The three oils were evaluated for their in vitro herbicidal activity by determining their influence on the germination and the shoot and root growth of the four weed species Sinapis arvensis L., Lolium rigidum Gaudin , Trifolium campestre Schreb ., and Phalaris canariensis L. At the highest doses tested (0.8 and 1.0 mg/ml), the leaf essential oil inhibited either totally or almost completely the seed germination and the shoot and root growth of S. arvensis and T. campestre. The oils were also tested for their antifungal activity; however, their effects on the fungal growth were statistically not significant.     

Chemical Composition and Antimicrobial Activities of Essential Oils of Laggera pterodonta Collected in Four Different Locations in Yunnan,China*

Essential oils obtained by hydrodistillation from leaves of Laggera pterodonta collected from four different locations (Kunming, Lijiang, Puer and Xinping) in Yunnan, China, were analyzed using GC MS and GC FID. The number of compounds identified in each sample was 39, 37, 33 and 44, respectively, representing 9332% (Kunming), 8057% (Lijiang), 9224% (Puer) and 9385% (Xinping) of total essential oils. Chemical compositions of essential oils differed between sample locations: thus, those from Kunming were rich in benzenoid compounds (3806%) while those from Lijiang and Puer were largely dominated by sesquiterpenes (1989% and 4465% respectively) and sesquiterpenes oxide (4085% and 3511%, respectively), and those from Xinping contained a high proportion of monoterpene hydrocarbons and sesquiterpene hydrocarbons (4223% and 3325% respectively) (7548%). The results of tests on the antimicrobial activities of essential oils indicated that chemical composition was affected by environmental variation causing differences in sensitivity to microbes among samples.     

Aroma volatiles of Cynara scolymus and Helianthus tuberosus

Samples of the aroma volatiles of globe artichoke and Jerusalem artichoke were obtained by well established methods and were analysed by routine GC and GC/MS. Eight sesquiterpene hydrocarbons afforded the major group of components (over 42%) in globe artichoke samples, with β-selinene (ca 32%) as the main constituent. Previously reported caryophyllene could not be detected. α-Cedrene was found to have globe artichoke aroma characteristics on odour evaluation of separated components at an odour port at the exit of the GC column. Jerusalem artichoke samples contained one major component (β-bisabolene, ca 51%) and a range of saturated long-chain hydrocarbons (ca 22%). The sesquiterpene presumably contributes appreciably to the characteristic flavour of Jerusalem artichoke. Both types of artichoke gave a low concentration of total volatiles.