Chemotaxonomic study on Thymus villosus from Portugal

The composition of the essential oils of four populations of Thymus villosus subsp. lusitanicus (Boiss.) Coutinho from Portugal was investigated by GC and GC-MS. To study the chemical polymorphism the results obtained from GC analyses of the volatile oils from individual plants from four populations were submited to Principal Component and Cluster analyses. A comparision with the essential oil of T. villosus subsp. villosus, previously studied by us was done. Important differences with regard to the major constituents in these two taxa were found. Linalool, geranyl acetate, geraniol and terpinen-4-ol were the main components of the essential oils of T. villosus subsp. lusitanicus, whereas in the oil of T. villosus subsp. villosus p-cymene, myrcene and alpha-terpineol were the major ones. Although, both taxa showed chemical polymorphism, different types of essential oils were characterized in each one: linalool; linalool/ terpinen-4-ol/trans-sabinene hydrate; linalool/1,8-cineole; geranyl acetate/geraniol; geranyl acetate/geraniol/1,8-cineole in T. villosus subsp. lusitanicus and p-cymene/camphor/linalool; p-cymene/borneol; linalool/geraniol/geranyl acetate; alpha-terpineol/camphor/myrcene in T. villosus subsp. villosus. Thus, the two subspecies of T. villosus can be easely differenciated by the composition of their essential oils.     

Screening of antibacterial activities of twenty-one oxygenated monoterpenes

Plant essential oils are widely used as fragrances and flavours in the cosmetic, perfume, drug and food industries. Oxygenated monoterpenes are widespread components of the essential oils, usually occurring in high amount. In this paper, the antibacterial activities of twenty-one oxygenated monoterpenes (borneol, borneol acetate, camphor, carvone, 1,8-cineole, citronellal, beta-citronellol, dihydrocarvone, fenchol, fenchone, geraniol acetate, isomenthol, limonene oxide, linalool, linalool acetate, nerol, nerol acetate, terpinen-4-ol, alpha-terpineol, menthol and menthone) and penicillin (standard antibiotic) were determined using a disc diffusion method (in vitro) against 63 bacterial strains, belonging to 37 different genera and 54 species (plant, food and clinic origins). The results showed that the oxygenated monoterpenes exhibited a variable degree of antibacterial activities. These compounds also inhibited the growth of bacterial strains by producing a weak zone of inhibition from 7 to 11 mm in diameter, depending on the susceptibility of the tested bacteria. Among the tested compounds, nerol, linalool alpha-terpineol, fenchol and terpinen-4-ol showed antibacterial activity at a broad spectrum. However, their antibacterial activities were lower than those of penicillin. In contrast to these compounds, camphor and 1,8-cineole exhibited no inhibition effects on the growth of all tested bacteria.     

Chemical composition of volatiles from cortical oleoresin of Pseudotsuga menziesii

Pseudotsuga menziesii cortical oleoresin was found to contain 1·7% of oxygenated terpenoids and compounds of similar volatility composed of linalool, methylsalicylate, bornyl acetate, citronellol, geranyl acetate, methylthymol, citronellyl acetate, terpinen-4-ol, borneol, isopulegol, anethole, terpinen-4-ol acetate, camphor, geraniol, neryl acetate, and nerol. Sesquiterpenoid hydrocarbons were low (only 0·07%) and contained sibirene and longifolene as main constituents, with β-caryophyllene, γ-muurolene, γ-cadinene (identified by IR), and 20 additional compounds in small amounts. p-Cymen-8-ene was identified in monoterpene hydrocarbon fraction.     

Volatile oil variability in Thymus serpylloides ssp. gadorensis growing wild in Southeastern Spain

Volatile oils from single plants of Thymus serpylloides ssp. gadorensis were collected from Southeastern Spain and studied to check for chemical variability using gas chromatography (GC) and gas chromatography-mass spectrometry (GC-MS). Many of the samples showed a phenolic chemotype, while another important group had significant levels of linalool. Geraniol, myrcene, caryophyllene oxide, terpinen-4-ol and 1,8-cineole were commonly present. Principal Component Analysis (PCA) and Cluster Analysis (CA) of this chemical variability separated two groups of plants characterized by either phenols or linalool, and an isolated third type with geraniol. A few samples were found to have both phenolic and non-phenolic compounds in high quantities, thus showing a mixed chemotype. Multidimensional scaling analysis (MDS) of the percentage concentration for each component of the essential oil showed that thymol, linalool, 1,8-cineole, borneol and geraniol have clear divergent vectors.     

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.     

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.     

In vitro antibacterial and cytotoxic activities of carvacrol and terpinen-4-ol against biofilm formation on titanium implant surfaces

Abstract

This study evaluated the antibacterial properties of carvacrol and terpinen-4-ol against Porphyromonas gingivalis and Fusobacterium nucleatum and its cytotoxic effects on fibroblast cells. The minimum inhibitory concentration (MIC) and the minimum bactericidal concentration (MBC) were examined. The minimum biofilm inhibition concentration (MBIC) was evaluated by XTT assay. Biofilm decontamination on titanium surfaces was quantified (CFU ml^?1), evaluated by confocal laser scanning microscopy (CLSM) and cytotoxic activity by MTT. The MIC and MBC for carvacrol were 0.007% and 0.002% for P. gingivalis and F. nucleatum, and 0.06% for terpinen-4-ol for both microorganisms. The MBIC for carvacrol was 0.03% and 0.06% for P. gingivalis and F. nucleatum, and for terpinen-4-ol was 0.06% and 0.24%. The results indicated anti-biofilm activity using carvacrol (0.26%, 0.06%) and terpinen-4-ol (0.95%, 0.24%) and showed cytotoxic activity similar to chlorohexidine (CHX). However, terpinen-4-ol (0.24%) showed higher cell viability than other treatments. Carvacrol and terpinen-4-ol showed antibacterial activity in respect of reducing biofilms. Moreover, CHX-like cytotoxicity was observed.     

Electroantennogram responses of Douglas-fir seed chalcids to plant volatiles

Douglas fir seed chalcids females oviposit specifically into Douglas cones which they locate using olfactory and visual cues. We have tested whether this specialization was correlated with a specialized sensitivity towards cone volatiles. Field collected adults were presented a series of pure volatile chemicals. Electroantennogram responses (EAG) were recorded to generally occurring terpenoids and straight chain alcohols and aldehydes found in flowers and plant leaves. Monoterpenes identified in Douglas cone headspaces (alpha-pinene, beta-pinene, 3-thujene, alpha- and beta-phellandrene, gamma-terpinene and myrcene) elicited lower EAG responses than fatty acid derivatives corresponding to green odours. The EAG response profile of females differed significantly from that of males. Females were very sensitive to hexanol-1, heptanal, (Z)-3 hexenol-1, terpineol and terpinen-4-ol. Male responses were significantly higher to humid air, nerolidol, thujan-4-ol, hexanal, carvacrol, piperitone and farnesol. Several compounds (Z- verbenol, carvone, jasminol, geraniol, nerol and eugenol) elicited long lasting electrophysiological responses (over 5 s) in both sexes.     

Nematicidal and Propagation Activities of Thyme Red and White Oil Compounds toward Bursaphelenchus xylophilus (Nematoda: Parasitaphelenchidae)

The toxic and propagation effects on Bursaphelenchus xylophilus of 28 Thymus vulgaris red oil and white oil compounds were examined using direct contact and cotton ball bioassays. Results were compared with those of the trunk-injection nematicides emmamectin benzoate, levamisol hydrochloride and morantel tartrate. In direct contact bioassays, geraniol (LC₅₀, 0.47 mg/ml) was the most toxic compound, followed by thymol (1.08 mg/ml), carvacrol (1.23 mg/ml) and terpinen-4-ol (2.61 mg/ml). In cotton ball tests with 20 inactive compounds at 2 mg/cotton ball, p-cymene significantly inhibited propagation (propagation ratio [PR] 8), compared with the castor oil-ethanol-treated control (PR 56). Propagation stimulation was observed with (–)-caryophyllene oxide, (+)-ledene, (+)- and (–)-limonene, linalool oxide, β-myrcene, (–)-α-phellandrene, (+)-α-pinene and γ-terpinene (PR 63–100). The other 10 compounds exhibited low to moderate levels of propagation inhibition (PR 36–56). At 0.1 μg/cotton ball, emmamectin benzoate and morantel tartrate exhibited complete suppression of propagation, whereas a very low level of propagation inhibition was obtained from levamisol hydrochloride (PR 6). In conclusion, propagation-stimulating compounds can exist in plants in addition to nematicidal compounds, and careful use of plant preparations containing high quantities of these compounds is mandatory.     

国产野生薄荷挥发油化学组分变异及其化学型

采用气－质联用的方法,对国产野生薄荷（ＭｅｎｔｈａｈａｐｌｏｃａｌｙｘＢｒｉｑ．）居群的挥发油成分进行了分析,２２个样品可归纳为６个化学型：（１）薄荷酮－胡薄荷酮型（ｍｅｎｔｈｏｎｅ－ｐｕｌｅｇｏｎｅｔｙｐｅ）;（２）胡椒酮型（ｐｉｐｅｒｉｔｏｎｅｔｙｐｅ）;（３）氧化胡椒酮－氧化胡椒烯酮型（ｐｉｐｅｒｉｔｏｎｅｏｘｉｄｅ－ｐｉｐｅｒｉｔｅｎｏｎｅｏｘｉｄｅｔｙｐｅ）;（４）芳樟醇－氧化胡椒酮型（ｌｉｎａｌｏｏｌ－ｐｉｐｅｒｉｔｏｎｅｏｘｉｄｅｔｙｐｅ）;（５）香芹酮型（ｃａｒｖｏｎｅｔｙｐｅ）;（６）薄荷醇－乙酸薄荷酯型（ｍｅｎｔｈｏｌ－ｍｅｎｔｈｙｌａｃｅｔａｔｅｔｙｐｅ）。结合地理分布和薄荷属单萜类成分生物合成途径,对上述主要类型进行了讨论。     

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%).     

Leaf essential oil composition of three species of Myrcianthes from Monteverde, Costa Rica

To examine the chemical diversity of essential oils from Myrcianthes species (Myrtaceae) as well as potential chemotaxonomic relationships between them, the leaf essential oils of M. fragrans (Sw.) McVaugh, M. rhopaloides (Kunth) McVaugh, and an undescribed species, Myrcianthes 'black fruit', from Monteverde, Costa Rica, were isolated by hydrodistillation and analyzed by GC/MS. The most abundant components of the essential oil of M. fragrans were 1,3,5-trimethoxybenzene (15.7%), (Z)-hex-3-en-1-ol (10.0%), alpha-cadinol (10.4%), eudesma-4(15),7-dien-1beta-ol (9.0%), caryophyllene oxide (7.8%), and spathulenol (7.5%). The leaf oils of two different samples of Myrcianthes rhopaloides were quantitatively different with one sample composed mostly of linalool (17.7%), alpha-cadinol (14.4%), spathulenol (11.1%), tau-cadinol (9.6%), and 1-epicubenol (6.9%), and the other was made up largely of (E)-hex-2-enal (46.1%), 1,8-cineole (12.5%), linalool (9.1%), alpha-cadinol (6.7%), and alpha-terpineol (4.4%). The major components in the leaf essential oil of Myrcianthes 'black fruit' were 1,8-cineole (38.3%), alpha-terpineol (21.2%), heptan-2-ol (15.5%), terpinen-4-ol (4.2%), and beta-pinene (3.8%). The leaf oil compositions of Myrcianthes in this study are very different from leaf oils from other members of Myrcianthes reported in the literature. A cluster analysis reveals large chemical variation not only between members of the genus, but also between samples of the same species.     

Influence of environmental and genetic factors on the stability of essential oil composition of Thymus pulegioides

Thymus pulegioides plants were collected from various natural habitats of Lithuania and transferred into a new uniform environment. The plants were cloned annually at controlled conditions and their essential oil composition was monitored by capillary GC and GC/MS. The geraniol/geranial/neral (G/G/N), thymol (T), linalool (L), carvacrol/γ-terpinene/p-cymene (C/γT/pC) and thymol/carvacrol/γ-terpinene/p-cymene (T/C/γT/pC) chemotypes of T. pulegioides were studied. It was found that according to the stability of essential oil composition on a sudden change of environmental conditions two types of T. pulegioides can be distinguished: (1) plants which preserve their chemical composition of the essential oils; (2) plants, which considerably change their chemical composition of the essential oils.     

Analysis of the volatile components of Lavandula canariensis (L.) Mill., a Canary Islands endemic species,growing in Australia

The essential oil of a Canary Islands endemic species, Lavandula canariensis (L.) Mill., gathered from Australia, was extracted by hydrodistillation and solid phase micro-extraction (SPME). The oils have been studied by GC and GC–MS. A total of 38 compounds have been identified in the leaf oil extracted by hydrodistillation, the principal components being carvacrol (23.6%), β-bisabolene (20.8%), (E,E)-α-farnesene (11.3%), β-caryophyllene (7.6%) and carvacrol methyl ether (7.3%), while the oil extracted by SPME showed carvacrol (42.6%) as the principal component with moderate amounts of (E,E)-α-farnesene (9.1%), β-bisabolene (7.5%), cis-hex-3-en-1-ol (5.6%) and carvacrol methyl ether (4.6%). SPME extracts indicated that carvacrol, cis-hex-3-en-1-ol and linalool were in greater concentration in the head space vapours than in the oil. This is the first report describing the essential oil composition of this species.     

Use of gas chromatograms of essential leaf oils to compare eight taxa of genus Angophora (Myrtaceae): possible relationships to the genus Eucalyptus

Essential oils were extracted from leaves of eight taxa of the genus Angophora, and then analysed. As expected the individual components of these oils were essentially the same as those found in the Eucalyptus species of our earlier studies (Bignell et al., 1997b. Flavour Fragrance J. 12, 423-432). In addition, as is also the case with the bloodwood eucalypts, only relatively low yields of oil were obtained. In all cases the Cineole component was extremely small, but the oils of six of the eight contained very large concentrations of the sesquiterpene Bicyclogermacrene. A table of the 52 major oil components is included. Principal components analysis (PCA) was performed on the gas chromatograms (GC) of the essential oils and the resulting scores plots compared with the cladistic classification of Thiele and Ladiges (1988). Cladistics 4, 23–42). Because of the close relationship between genus Angophora and Eucalyptus ‘subgenus’ Corymbia, the GC data for the eight Angophora taxa were combined with corresponding data for eleven randomly chosen taxa from ‘subgenus’ Corymbia (Bignell et al., 1996b, Flavour Fragrance J. 11, 339–347; 1997a, Flavour Fragnance J. 12, 277–284) and a PCA performed on the total system.     

Composition and Chemical Variability of the Essential Oil from Aerial Parts of Cladanthus scariosus,an Endemic Species to the Moroccan High Atlas

Cladanthus scariosus (Ball) Oberpr. & Vogt is endemic to Moroccan High Atlas. It is known under the vernacular names Irezghi or Irezgui. Three essential oil samples have been isolated from aerial parts and analyzed by combination of chromatographic and spectroscopic techniques [gas chromatography (GC) in combination with retention indices (RI), gas chromatography-mass spectrometry (GC/MS) and ¹³C-NMR spectroscopy]. The compositions of oil samples were dominated by monoterpenes: α-pinene sabinene, and terpinen-4-ol. Chamazulene and dihydrochamazulene isomers as well as various hemiterpene esters and analogs have been identified. To evidence a chemical variability, statistical analysis performed on 13 oil sample compositions allowed partitioning into three groups, mainly differentiated by their contents of sabinene, camphor, borneol, terpinen-4-ol, and germacrene D.     

Chemical composition of the essential oils of two Rhodiola species from Tibet

The essential oils from rhizomes of Rhodiola crenulata and R. fastigiata in eastern Tibet were analyzed by using GC-MS. The major constituents were geraniol (53.3%), n-octanol (13.4%), 2-methyl-3-buten-2-ol (10.8%), citronellol (5.3%), 3-methyl-2-buten-1-ol (4.0%), myteol (3.0%), and linalool (2.4%) for R. crenulata and geraniol (45.3%), n-octanol (12.3%), 2-methyl-3-buten-2-ol (8.0%), linalool (5.1%), isogeraniol (4.5%), citronellol (4.4%), and cis-sabinenehydrate (3.6%) for R. fastigiata.     

Behavioural and electrophysiological responses of Pantomorus cervinus (Boheman) (Coleoptera: Curculionidae) to host plant volatiles

Abstract  Fuller's rose weevil (FRW; Pantomorus cervinus ) (Coleoptera: Curculionidae), a polyphagous pest of citrus and other horticultural plants, was studied in laboratory assays designed to identify potential semiochemicals from host plants that might be exploited for weevil pest management. Using still-air bioassays, weevils were found to be most attracted to fresh whole lemon leaves compared with cut and/or dried lemon leaves. White clover, an understorey plant in kiwifruit orchards, was also found to be attractive to weevils in the dual-choice tests. Coupled gas chromatography-electrophysiological recording of weevil antennal responses to commercial extracts of lemon leaves indicated that weevils detected at least eight monoterpene components of the oil, i.e. linalool, terpinen-4-ol, nerol, neral, geraniol, geranial, neryl acetate and geranyl acetate. Significant antennal dose–responses were evident to lemon leaf oil, lemon constituent odours and two major green leaf volatiles detected from clover ( Z )-3-hexenol and ( Z )-3-hexenyl acetate. Still-air dual-choice tests on individual chemicals showed significant repellency from seven of the lemon leaf compounds at 500 µg/100 µL (all except geranyl acetate). Weevils were attracted to a synthetic blend consisting of the green leaf volatiles over a range of concentrations (1, 10 and 100 mg/100 µL), as well as to clover leaves. These plant kairomone components may be potentially useful as repellents or attractants for FRW control and management programme.     

Constituents of Cold-Pressed Peel Oil of Citrus natsudaidai Hayata

A study was made on the elaborate separation and identification of the fraction, boiling higher than monoterpene hydrocarbons, of cold-pressed peel oil of Citrus natsudaidai Hayata, by using fractional distillation under reduced pressure, adsorption and gas chromatography, infrared, mass and proton magnetic resonance spectrometry. The following components were identified; in sesquiterpene hydrocarbon series: copaene, β-elemene, β-ylangene, caryophyllene, aromadendrene, farnesene, α-selinene, δ-cadinene, calamenene, α-calacorene; and among oxygenated compounds: n-nonyl alcohol, n-decyl alcohol, linalool, α-terpineol, terpinen-4-ol, nerolidol, elemol, n-octyl aldehyde, n-decyl aldehyde, perillaldehyde, carvone, n-octyl acetate, n-decyl acetate, geranyl acetate, perillyl acetate and acetic ester of p-methadiene-1,8(10)-ol-9.     

Effect of seasonal climatic changes on biomass yield and terpenoid composition of rose-scented geranium (Pelargonium species)

Variations in biomass yield, essential oil yield and terpenoid composition in rose-scented geranium (Pelargonium species) in response to seasonal climatic changes were investigated under semiarid tropical climatic conditions. A large number of essential oil samples were collected during different seasonal months (once a month) and daily during the peak summer season months of May and June. They were analysed for terpenoid composition by GC and GC-MS. The crop yielded the lowest values for biomass yield, essential oil yield and essential oil concentration in the summer months of April to June. Evaluation of terpenoid compositions showed minimum concentrations (% of essential oil) of linalool, geraniol and its esters and maximum concentrations of citronellol and its esters during summer months. The percentages of geraniol and its esters were highest during cool winter season months of December and January followed by rainy and autumn season months. Isomenthone, 10-epi-gamma-eudesmol and other minor terpenoid compounds (present in <1% amounts in the essential oil) did not exhibit any definite seasonal trends. Rainy/monsoon (August and September) and autumn (October and November) season months were characterised by high rainfall, cloudy days and short photoperiods. These favourable environmental conditions encouraged crop growth and produced highest biomass yields, essential oil yields and maximum concentration of essential oil in rose-scented geranium plants.