Variability in essential oil composition of Piper dilatatum L.C. Rich

Twelve samples of air-dried aerial parts of Piper dilatatum L. C. Rich yielded essential oils and their volatile constituents were analyzed by GC and GC–MS. Sesquiterpenes, both hydrocarbons and oxygenated, were the most highly represented classes, the former ranging from 31.5% to 87.7% and the latter varying from 1.8% to 49.4%. Using hierarchical cluster analysis, the oils were divided into seven groups, whose main constituents were: (E)-caryophyllene, α-cadinol and germacrene D (group A); spathulenol, bicyclogermacrene and (Z)-β-ocimene, (group B); spathulenol, germacrene D and (E)-nerolidol, (group C); germacrene D, limonene, α-phellandrene and bicyclogermacrene (group D); β-elemene, germacrene D and β-pinene (group E); curzerene, p-cymene and α-eudesmol (group F); and (Z)-α-bisabolene, curzerene and germacrene D (group G). We have seen that Piper oils from the Amazon present as major constituents terpenoids and phenylpropanoids, always with the predominance of one over another. The essential oils of P. dilatatum presented in this paper, containing only mono- and sesquiterpenes as its major components, is further chemotaxonomic evidence of this dichotomy in the Piper genus.     

Essential oils of Phlomis leucophracta,Phlomis chimerae and Phlomis grandiflora var. grandiflora from Turkey

The essential oils of three species of Phlomis from Turkey, Phlomis leucophracta, Phlomis chimerae and Phlomis grandiflora var. grandiflora have been studied. The main constituents of P. leucophracta essential oil were β-caryophyllene (20.2%), α-pinene (19.2%) and limonene (11.0%). This species also contained three diterpene derivatives, 15-isopimaradiene, manoyl oxide and epi-13-manoyl oxide that summed 1.4%. In P. chimerae the principal compounds were β-caryophyllene (31.6%), α-pinene (11.0%), germacrene D (6.1%), limonene (5.5%) and linalool (4.7%). In P. grandiflora var. grandiflora, germacrene D (45.4%), β-caryophyllene (22.8%) and bicyclogermacrene (4.9%) were among the principal derivatives.     

GC-MS analysis of the essential oils of Juniperus communis L. berries growing wild in the Molise region: Seasonal variability and in vitro antifungal activity

Juniperus communis L., also known as the common juniper, is a dioecious aromatic evergreen shrub and has been traditionally used in many countries as a diuretic, antiseptic, and digestive and as a flavor to aromatize certain alcoholic beverages. We analyzed the chemical variability in the volatile profiles from berries of J. communis, harvested in one of the oldest European parks, the National Park of Abruzzo, Lazio, and Molise (PNALM, Central Italy). We examined the berries in different phases of the biological cycle for 1 year (at six ripening stages). Hydrodistilled essential oils from the fresh berries were analyzed by gas chromatography–flame ionization detection (GC-FID), gas chromatography–mass spectrometry (GC-MS) and principal component analysis (PCA). A total of 90 components were detected, and remarkable qualitative and quantitative differences were observed in the chemical components during the ripening stages, from the green unripe berries to the bluish-black berries harvested at full maturity. The essential oils were an α-pinene (13.43–32.34%) chemotype. The monoterpene hydrocarbons decreased during the ripening with a progressive increase in sesquiterpenes such as germacrene D (12.29–17.59%) and β-caryophyllene (7.71–8.51%), which are the major components in ripe berry essential oils. The sesquiterpene hydrocarbon fraction (65.3–47.9%) also contained α-humulene, germacrene B, δ-cadinene, bicyclogermacrene, and eudesma 4(14),11 diene. Germacrene D and β-caryophyllene in high concentrations may be considered as marker components of the genus Juniperus from the Molise region. This particular chemical composition has been reported for the first time. It is interesting to note the presence of β-caryophyllene (7–11%), whose inhalation has been reported to affect anxiety and depression in a rat model. An in vitro antifungal assay showed that the essential oil from green and ripe berries inhibits the growth of Sclerotium rolfsii, a phytopathogen fungus that causes post-harvest diseases in many fruits and vegetables.     

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.     

The leaf oil terpene composition of Juniperus occidentalis

The chemical composition of the volatile oil of 10 trees each of two Oregon populations of the western juniper was determined by a computerized GC-MS method. The identity of the major components, sabinene, α-pinene, α- and γ-terpinene, p-cymene, limonene, terpinen-4-ol and bornyl acetate was confirmed. In addition, tricyclene, α-thujene, camphene, β-pinene, α- and β-phellandrene, car-3-ene, trans-ocimene, linalool oxide, terpinolene, trans-sabinene hydrate, camphor, camphene hydrate, borneol, α-terpineol, p-cymenol, methyl citronellate, citronellyl acetate, carvacrol, cuminic aldehyde, β-bourbonene, several cadinene and cadinol isomers, elemol, γ-, β- and α-eudesmol, and manoyl oxide were identified. Santene, citronellol, and aromatic ethers of the safrole-eugenol type were not found. Tree-to-tree variability of the relative percentages of these terpenes was fairly large and chemosystematic implications are discussed briefly.     

Identification des constituants de l'essence des aiguilles de Pinus pinaster

The chromatographic analysis of the volatile leaf oil of Pinus pinaster Ait. showed 42% of monoterpene hydrocarbons (α-pinene, camphene, β-pinene, myrcene, 3-carene, limonene, cis-ocimene, terpinolene, para-cymene, 35% of sesquiterpene hydrocarbons (cubebene, copaene, caryophyllene, humulene, germacrene D, α- and γ-muurolenes, δ- and γ-cadinenes) and 23% of oxygenated compounds including esters (linalyl, bornyl, geranyl, neryl and farnesyl acetates), alcohols (cis-hexenol, linalool, α-fenchol, trans-pinocarveol, terpinen-4-ol, α-terpineol, dihydrocarveol, guaiol, junenol and α-cadinol), one aldehyde (hexenal) and one ketone (piperitone). Three non terpenoid phenylethyl esters were also identified: phenylethyl isovalerate, methyl-2 burtyate and 3-3 dimethylacrylate. Some alcohols and mainly α-terpineol and linalool seemed to be formed during the steam distillation process, they were absent when the leaf oil was obtained by maceration of small portions of leaves in the usual solvents of terpenes.     

The Chemical Constituents of the Essential Oil from the Flowers,Leaves and Peels of Citrus aurantium

Citrus aurantium L. var. amara Engl., is a better species of sour oranges. There are essential oils in the flowers, the peels, the leaves and the branches of C. aurantium. The flower oil can be used in the preparation of perfumes of high quality. The peel oil is used mainly for the flavor-endowing of soft drinks, alcoholic drinks, bread, confectionaries and cakes. In order to control the quality of the essential oils and to improve them, we have systema- tically studied the chemical constituents of the flowers, the leaves and the peals of C. aurantium with our preparation. 12 main components were separated by silica gel column chromatography. The following 33 chemical components were identified by IR, GC-MS and GC retention index: α-thujene, α-pinene, camphene, β-pinene, myrcene, limonene, β-ocimene, trans-linalooloxide (furanoid), cis-linalooloxide (furanoid), linalool, 1,4-p-methadien-7-ol, trans-pinocarveol, camphor, terpinen-4-ol α-terpineol, nerol, citral-b, geraniol, linalylacetate, citrala, trans-linalooloxide (pyranoid), methyl anthranilate, terpinyl acetate, cis-linalooloxide (pyranoid), neryl acetate. geranyl acetate, nonanal, β-caryophyllene, α-humulene, γ-muurolene, β-nerolidol, farnesol, α- nerolidol. GC retention index of 33 compounds were measured. A fast method for routine determination is presented.     

Studies on Chemical Constituents of the Essential Oil of Artemisia subdigitata Mattf by Glass Capillary Gas Chromatography

subdigitata Mattf. by glass capillary gas chromatography. Their oils were determined by retention time, standard addition method and GC-MS. 15 components have been identified i.e. α-thujene, α-pinene, camphene, sabinene, β-pinene, myrcene, δ-3-carene, β-ocimene-x, β-isopropyl phenol, limonene, γ-terpinene, terpinen-4-ol, estragolc, geraniol, methyl eugenol. Their contents have been determined.     

Essential oil variation in Calyptranthes spruceana

Two chemical races in Calyptranthes spruceana were examined. One of them contains limonene, geranial and perillaldehyde as the main constituents of its essential oil. The other is shown to contain α-pinene, β-pinene, neral and geranial as its major oil components.     

Essential oil of Stachys aleurites from Turkey

The essential oil obtained from the aerial parts of the Turkish endemism Stachys aleurites (Lamiaceae) has been studied. The main constituents were sesquiterpene hydrocarbons: β-caryophyllene (33.7%), bicyclogermacrene (14.5%) and germacrene D (9.6%). The main monoterpene was α-pinene (8.4%). Some chemotaxonomical considerations have been provided.     

Studies on Leaf Oils of Citrus Species

Leaf oil samples of four Japanese citrus species were analysed by gas chromatography to determine the detailed composition of each leaf oil. The following components were identified: α-pinene, α-thujene, camphene, β-pinene, sabinene, β-myrcene, α-terpinene, limonene, β-phellandrene, trans-2-hexen-1-al, γ-terpinene, p-cymene, terpinolene, cis-2-penten-1-ol, n-hexyl alcohol, cis-3-hexen-1-ol, trans-2-hexen-1-ol, p-α-dimethylstyrene linalool, linalyl acetate, β-elemene, terpinen-4-ol, caryophyllene, humulene, α-terpineol, neryl acetate, geranyl acetate, β-selinene, geraniol and thymol. Most components were contained in common in leaf oils of the four citrus species, but relative contents of some of the components; such as γ-terpinene, linalyl acetate, and thymol differed from species to species. For example, γ-terpinene was the major component (33.8%) of Hassaku, whereas it was only a minor component in Daidai. Daidai is characterized by a very high content of linalyl acetate (35%) which is only a trace in the other three species. Kishu-mikan is characterized by a high content of thymol (15%).     

Survival in different habitats: Extreme ultramafic and calcareous soils affect Stachys recta essential oils composition

Two populations of Stachys recta growing in Italy on ultramafic and calcareous soils have been studied for their essential oils. Although the yields were comparable, the composition of the essential oils differed significantly. Plants growing on ultramafic soil produced mainly non-terpene derivatives (55.7%), of which the most abundant ones were 1-octen-3-ol (38.2%) and (E)-3-hexen-1-ol (5.9%); the terpenes α-cadinol (6.1%) and δ-cadinene (5.6%) were also significantly represented. In contrast, the populations living on calcareous soil produced an essential oil dominated by terpenes (93.8%), with germacrene D (18.8%), β-caryophyllene (17.7%), 1,8-cineole (15.9%) and α-pinene (14.2%) among the main components.     

Volatile compounds from some wild growing aromatic herbs of the Lamiaceae from southern France

Abstract

The composition of the volatile fraction in selected aromatic plants of the Lamiaceae from garrigue sites in southern France is described. Calamintha nepeta appeared heterogeneous. The oil was dominated by piperitone oxide, and piperitenone oxide or by pulegone and menthone. In Nepeta nepetella, nepetalactone, almost exclusively the (4a-α, 7α, 7a-β)-isomer, made up more than 85% of the essential oil. Dichloromethane extracts from Teucrium polium contained germacrene D or sabinene as main components, α-pinene, β-pinene and β-caryophyllene in varying proportions as further important constituents, and various minor components depending on the origin.     

Volatile composition and antimicrobial activity of twenty commercial frankincense essential oil samples

Trees from the genus Boswellia (Burseraceae) are traditionally used as a medicine, a fumigant, in various cosmetic formulations and in aromatherapy in several countries around the world. This plant produces a commercial oil known as frankincense which has a woody, spicy and haunting smell. Frankincense oil has several pharmacological properties, of which many elude to the anti-infective potential. Variation in the chemical composition of this oil has been reported in literature. These factors prompted an investigation to study the commercial frankincense oils from various international suppliers. Twenty essential oils were analyzed by gas chromatography coupled to mass spectrometry. Considering the major constituents, the oils were found to be qualitatively similar. However, there was immense quantitative variation for certain oil constituents. The components identified and their range in the oils include α-pinene (2.0–64.7%); α-thujene (0.3–52.4%); β-pinene (0.3–13.1%); myrcene (1.1–22.4%); sabinene (0.5–7.0%); limonene (1.3–20.4%); p-cymene (2.7–16.9%) and β-caryophyllene (0.1–10.5%). The antimicrobial activity (minimum inhibition concentration assay) of the oils was investigated against five reference test organisms and the activity ranged from 4–16 mg/ml (Staphylococcus aureus); 1.5–8.3 mg/ml (Bacillus cereus); 4.0–12.0 mg/ml (Escherichia coli); 2.0–12.8 mg/ml (Proteus vulgaris) and 5.3–12.0 mg/ml (Candida albicans).     

Studies on the Chemical Constituents of the Hydrocarbon Fraction of the Essential Oils from Caryopteris tangutica and C. Glutinosa

The chemical constituents of the hydrocarbon fraction of essential oils of Caryopteris tangutica Maxim. and C. glutinosa Rehd were examined by means of GC-MS-COM and GC retention time data on a 45 m capillary column coated with OV- 101. 21 components have been saparated and identified, i.e. α-thujene, α-pinene, cam- phene, sabinene, β-pinene, β-myrcene, α-terpinene, p-cymene, limonene, β-ocimene-y, β- phellandrene, α-terpinolene, α-cubebene, α-copaene, α-cedrene, β-caryophyllene, γ-cadinene, 1-aromadendrene, α-humulene, β-bisabolene and δ-cadinene. The quantitative determination of these components was carried out by GLC also.     

Phenological variations of secondary metabolites from Hypericum triquetrifolium Turra

The essential oils and phenolic constituents from the aerial parts of Hypericum triquetrifolium Turra, were analyzed at three developmental stages (vegetative, flowering and fruiting stages). The highest content of oil (0.12% w/w) was obtained at full flowering. Whatever the analyzed stage, n-octane, α-pinene, β-caryophyllene, 2-methyloctane, n-nonane, α-longipinene, caryophyllene oxide and β-pinene were found to be the main compounds. However, their percentages varied with the phenological cycle. Analysis by RP-HPLC-DAD of the methanolic extracts enabled us to identify 14 phenolic components and rutin, hyperoside, quercitrin and quercetin were reported as the main components. With the exception of chlorogenic acid, kaempferol and amentoflavone, the content of the remaining identified phenolic components varied with the phonological cycle.     

Dr. Alfred Jeske 75 jahre

The chemical composition, phytotoxic and antifungal activities of the essential oils isolated by hydrodistillation from the needles of Tunisian Aleppo pine harvested from different provenances were evaluated. The chemical composition analysed by gas chromatography/mass spectrometry (GC/MS) revealed variability among provenances displaying interesting chemotypes, (Z)-caryophyllene (16.16–28.9%), β-myrcene (8.5–22.9%), α-pinene (11.7–13.14%), β-pinene (3.13–11.8%), bicyclogermacrene (5.2–12.37%), α-terpinolene (8.11–11.01%) and α-humulene (2.85–5.2%), which were the main components in the oil. Antifungal ability of Aleppo pine oils was tested by disc agar diffusion against 10 phytopathogenic fungi. Weak antifungal activity was observed for the essential oils isolated. Furthermore, in contrast, the herbicidal activity investigated for three common weeds in Tunisian cereal crops was very strong and seed germination was inhibited at a low concentration and their herbicidal effects were higher than those of a commercial herbicide.     

Repellent Efficacy of Caraway and Grapefruit Oils for Sitophilus oryzae (Coleoptera: Curculionidae)

This study examined the repellent efficacy of six essential oils extracted from caraway, clary sage, grapefruit, strawberry, thyme white, ylangylang, and their related volatile constituents against the adult rice weevil, Sitophilus oryzae using an olfactometer. The caraway and grapefruit oil showed the highest repellent efficacy against the rice weevil at a dose of 10μl. Gas Chromatography-Mass Spectrophotometer analysis revealed caraway oil to be rich in carvone and limonene, and grapefruit oil to be rich in limonene, β-myrcene and α-pinene. When the monoterpene was mixed in equal parts with the caraway and grapefruit essential oils, carvone with limonene in caraway oil demonstrated the highest repellent efficacy (96.7%). Limonene with α-pinene and β-myrcene in grapefruit showed strong repellent efficacy (86.4%) with synergistic effects on the S. oryzae.A mixture of caraway and grapefruit oils, as well as carvone and limonene, can be potent repellents that may be useful for controlling S. oryzae.     

Chemical Studies on the Essential Oils of Foeniculum vulgare

Twenty seven chemical constituents of oils from sweet leaves, flowers and fruits of Foeniculum vulgare Mill. are examined by GC and GC-MS with both different chromatographic columns. They are 1,1-diethoxyethane, α-thujene, α-pinene, camphene, sabinene, β-pinene, myrcene, α- phellandrene, p-cymene, limonene, cineole, γ-terpinene, fenchone, camphor, terpinen-4-ol, α-terpineol, estragole, verbenone, fenchol acetate, carveol, trans-fenchol acetate, carvone, anethole, anisaldehyde, trans-anethole, methoxyphenyl acetone and benzoic acid, 4-methoxy-, othylester. The limonene is 57.8% in the essential oil from leaves, 34.2% from flowers, 13.1% from fruits, The trans-anethole is 21.8% in the essential oil from leaves, 41.2% from flowers, 63.4% from fruits.     

马尾松枝条挥发性组分的鉴定及松墨天牛对其触角电生理反应

为研究松墨天牛Monochamus alternatus Hope取食期引诱剂,利用气相色谱-质谱(GC-MS)联用技术并与标样核对分析了马尾松(Pinus massoniana Lamb.)枝条挥发性气味的化学组成。结果表明,马尾松1年生、2年生、3年生枝条气味均由8种萜烯类物质组成,但各组分相对含量不同。经方差分析,α-蒎烯、莰烯、β-蒎烯、柠檬烯、萜品油烯、β-石竹烯在3种枝条中的相对百分含量的差异均达到极显著水平。1年生枝条中α-蒎烯、莰烯和萜品油烯的相对含量最小,分别为20.81%、0.43%和4.74%,而β-蒎烯、月桂烯和柠檬烯的相对含量最高,分别为12.37%、4.33%和4.53%。鉴定的化合物对松墨天牛雌雄成虫的触角电生理反应的实验,结果表明,松墨天牛雌雄成虫对α-蒎烯的反应最强,对β-石竹烯的反应最弱。