Chemical compositions,antimicrobial and herbicidal effects of essential oils isolated from Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum

The chemical composition of essential oils isolated from the aerial parts by hydrodistillation of Turkish Tanacetum aucheranum and Tanacetum chiliophyllum var. chiliophyllum were analyzed by GC–MS. The oils contain similar major components. The major components of T. aucheranum oil were 1,8-cineole (23.8%), camphor (11.6%), terpinen-4-ol (7.2%), α-terpineol (6.5%), borneol (3.8%), (E)-thujone (3.2%), epi-α-cadinol (3.1%), and artemisia ketone (3.0%). Camphor (17.9%), 1,8-cineole (16.6%) and borneol (15.4%) were found to be predominant constituents in the oil of T. chiliophyllum. It is interesting to find that ester derivatives of dihydro-α-cyclogeranic acid (2,2,6-trimethylcyclohexylcarboxylate), dihydro-α-cyclogeranyl hexanoate (10.1%), dihydro-α-cyclogeranyl pentanoate (3.0%), dihydro-α-cyclogeranyl butanoate (2.1%) and dihydro-α-cyclogeranyl propionate (1.2%) are firstly found as chemotaxonomically important components in T. chiliophyllum oil. From these, dihydro-α-cyclogeranyl hexanoate was isolated on silica gel column chromatography and its structure was confirmed by spectroscopic methods. This is the first report on the occurrence of ester derivatives of dihydro-α-cyclogeranic acid in essential oils of Tanacetum species. The oils were also characterized to have relatively high amounts of oxygenated monoterpenes. Results of the antifungal testing by microbial growth inhibition assays showed that the oils completely inhibit the growth of 30 phytopathogenic fungi. However, their growth inhibition effects were lower than commercial benomyl. The oils tested for antibacterial activity against 33 bacterial strains showed a considerable antibacterial activity over a wide spectrum. Herbicidal effects of the oils on seed germination of Amaranthus retroflexus, Chenopodium album and Rumex crispus were also determined and the oils completely inhibited the seed germination and seedling growth of the plants.     

Diterpene esters of aristolochic acids from Aristolochia pubescens

From the acetone and ethanol extracts of the tubercula of Aristolochia pubescens, two diterpene esters of aristolochic acids were isolated, together with 23 known compounds. The structures of the compounds were determined on the basis of spectroscopic analysis.     

GC-MS analysis of the essential oils, and the isolation of phenylpropanoid derivatives from the aerial parts of Pimpinella aurea

A combination of vacuum liquid chromatography (VLC) and preparative thin layer chromatography (PTLC) of the dichloromethane extract of the aerial parts of the Iranian plant Pimpinella aurea afforded two phenylpropanoids, erythro-1'-(4-methoxyphenyl)-propan-1',2'-diol (1) and erythro-1'-[4-(sec-butyl)-phenyl]-propan-1',2'-diol (2), the latter being a natural product. The structures of these compounds were determined by spectroscopic means. The antioxidant properties of these compounds were assessed by the DPPH assay. The GC-MS analysis of the essential oils of P. aurea provided a chemical profile that was significantly different from the previously published reports.     

Wood essential oils of two endemic trees from New Caledonia: Callitris sulcata (Parl.) Schltr. and Callitris neocaledonica Dummer

The essential oils obtained by hydrodistillation of pieces of dead trunks of Callitris sulcata (Parlatore) Schlechter and Callitris neocaledonica Dummer were investigated by gas chromatography, mass spectrometry and NMR spectroscopy. Analyses evidenced the presence of rare natural compounds: both essential oils are exclusively sesquiterpenic with nevertheless remarkable difference: C. sulcata essential oil was dominated by β-barbatene and thujopsene while C. neocaledonica was characterized by high levels of guaiane- and eudesmane-type structures (eudesmols, guaiol and related components). The biochemical correlations between the major components of each species are discussed and the relationship between the two species is commented.     

Chemoprevention by thyme oils of Aspergillus parasiticus growth and aflatoxin production

The essential oils from Thymus eriocalyx and Thymus X-porlock obtained by hydrodistillation were analyzed by GC/MS. The major components of T. eriocalyx and T. X-porlock oils were thymol (63.8, 31.7%), beta-phellandrene (13.30, 38.7%), cis-sabinene hydroxide (8.1, 9.6%), 1,8-cineole (2, 1.7%), and beta-pinene (1.31, 2%), respectively. Antifungal activities of the oils were studied with special reference to the inhibition of Aspergillus parasiticus growth and aflatoxin production. Minimal inhibitory (MIC) and minimal fungicidal (MFC) concentrations of the oils were determined. Static effects of the above oils against A. parasiticus were at 250 ppm and lethal effects of T. eriocalyx and T. X-porlock were 500 and 1000 ppm of the oils, respectively. Aflatoxin production was inhibited at 250 ppm of both oils with that of T. eriocalyx being stronger inhibitor. Transmission electron microscopy (TEM) of A. parasiticus exposed to MIC level (250 ppm) of the oils showed irreversible damage to cell wall, cell membrane, and cellular organelles. It is concluded that the essential oils could be safely used as preservative materials on some kinds of foods at low concentrations to protect them from fungal infections.     

Biochemical activities of Iranian Mentha piperita L. and Myrtus communis L. essential oils

GC-MS analysis of essential oils of Iranian Mentha piperita and Myrtus communis extracted by hydrodistillation lead to identification of 26 and 32 compounds, respectively. The oils had good to excellent antimicrobial activities against Escherichia coli, Staphylococcus aureus and Candida albicans with the oil of M. piperita being more active. The findings suggest feasibility of application of M. piperita oil in treatment of the infections caused by C. albicans and E. coli. D-values on exposure to M. piperita and Myrtus communis oils were (2.14 and 2.8min), (1.4 and 12.8min) and (4.3 and 8.6min) for E. coli, S. aureus and C. albicans , respectively. The oils were screened for their possible antioxidant activities by two complementary test systems, namely DPPH free radical scavenging and beta-carotene/linoleic acid systems. M. piperirta oil exerted greater antioxidant activity than that of M. communis. Phytochemical and phytobiological characteristics of these oils may lead to extraction and production of active compounds in single or combined forms with useful applications.     

Essential oil composition of Hypericum L. species from Southeastern Serbia and their chemotaxonomy

The essential oils of the aerial parts of nine species of Hypericum (Hypericum barbatum, Hypericum hirsutum, Hypericum linarioides, Hypericum maculatum, Hypericum olympicum, Hypericum perforatum, Hypericum richeri, Hypericum rumeliacum and Hypericum tetrapterum), collected from different locations in Southeast Serbia, were obtained by steam distillation and analyzed by GC and GC–MS. The essential oils investigated were characterized by a high content of non-terpene compounds and a low content of monoterpenes. The contents of non-terpenes, monoterpenes and sesquiterpenes in oils of the species H. barbatum, H. richeri and H. rumeliacum (section Drosocaprium) were similar and these oils were characterized by high contents of fatty acids. The oils of H. hirsutum and H. linarioides (section Taeniocarpium) contained a high percentage of n-nonane. There were similarities in contents of non-terpenes and sesquiterpenes in oils of species that belong to the section Hypericum (H. maculatum, H. perforatum and H. tetrapterum). The oil of H. olympicum differed from others by higher terpene content. A comparison was also carried out of the chemical composition of the essential oils from flower, leaf and stem of H. perforatum and it revealed that the highest concentration of non-terpene compounds was found in the flower and stem oil, while a high concentration of sesquiterpenes was characteristic for leaf oil. There were significant differences in the concentrations of the same compounds in the essential oils of H. maculatum, H. olympicum and H. perforatum, collected in different years from the same location which could be explained by seasonal differences. All data were statistically processed with principal component analysis and cluster analysis. The main conclusion from the above data is that genetic and environmental factors both play a role in determining the composition of essential oils of the Hypericum species studied.     

Sterols and steryl esters in some Brassica and Sinapis seeds

The qualitative and quantitative composition of sterols in the free form and esterified to fatty acids was studied in seed oils from Brassica napus, B. campestris, B..iuncea, B. nigra, Sinapis alba and S. aruefisis (Brassica kaber). Sitosterol, followed by campesterol, predominated in both the free and the esterified sterols. The free sterols were richer in brassicasterol (ca 10–20%) than the steryl esters (3–10%). Small amounts of δ⁵-avenasterol and δ⁷-stigmastenol were also found in the Brassica oils, often more in the esterified than in the free form. The quantity of sterols was studied only in Brassica campestris, which had ca 0.3 % in the free as well as in the esterified form. In Sinapis alba, ca 10% of the sterols in the free form and 20 % in the esterified sterols were δ⁵-avenasterol. This compared to only a few per cent in both the free and esterified sterols in the Brassica oils. Similarly, ca 2 % of cholesterol was found among the sterols of Sinapis alba but only traces in the Brassica oils. The similarity of sterol compositions among the cultivated brassicas and wild mustard (Sinapis arvensis), and the specific characteristics of the sterols in white mustard (Sinapis alba) adds further weight to the suggestion that wild mustard should be treated as Brassica kaber and strengthens the generic separation of Sinapis alba.     

Stigmastane derivatives and isovaleryl sucrose esters from Vernonia guineensis (Asteraceae)

Vernoguinoside, 16beta,22R;21,23S-diepoxy-3beta-O-beta-D-glucopyranosyloxy-21S,24-dihydroxy-5alpha-stigmasta-8,14-dien-28-one (1), a new stigmastane derivative, 16beta,22R;21,23S-diepoxy-21S,24-dihydroxy-5alpha-stigmasta-8,14-diene-3,28-dione (2) and two new sucrose esters, 1',3,3',4',6'-pentakis-O-(3-methylbutanoyl)-beta-D-fructofuranosyl alpha-D-glucopyranoside (3) and 1',2,3',6,6'-pentakis-O-(3-methylbutanoyl)-beta-D-fructofuranosyl alpha-D-glucopyranoside (4), have been isolated from the stem bark of Vernonia guineensis. The structures of the new compounds were determined on the basis of spectroscopic evidence.     

Preparation of carboxylic acid-bearing polysaccharide nanofiber made from euglenoid β-1,3-glucans

This paper introduces a new strategy for creating surface modified polysaccharide nanofibers. To demonstrate proof of principle, the synthesis, structure, and self-assembly behavior of a carboxylic acid-bearing polysaccharide made from paramylon (β-1,3-glucan) and succinic anhydride were investigated. Examination by a combination of NMR, FT-IR, and SEC-MALLS confirmed that successful preparation of the desired succinylated paramylon without significant depolymerization. NMR, SEC-MALLS, visible absorption and CD spectroscopic analyses indicated that the paramylon derivative forms the triplex structure in solutions. SEM observation revealed that succinylated paramylon forms a nanofiber that has carboxylic acid on the surface.     

Composition and anti-plasmodial activities of essential oils from some Cameroonian medicinal plants

In a search for new plant-derived biologically active compounds against malaria parasites, five essential oils extracted from the Cameroonian plants Xylopia phloiodora, Pachypodanthium confine, Antidesma laciniatum, Xylopia aethiopica, and Hexalobus crispiflorus were evaluated in regard to their anti-plasmodial activity against the W2 strain of Plasmodium falciparum. The oils were obtained from the plants with 0.12, 0.13, 0.18, 0.6 and 0.1% yields (relatively to dried material weight) respectively. Analysis by gas chromatography and mass spectrometry identified mainly terpenoids, among which alpha-copaene, gamma-cadinene, delta-cadinene, alpha-cadinol, spathulenol and caryophyllene oxide were most commonly found. The five oils were active against Plasmodium falciparum in culture. The most effective was the oil of Hexalobus crispiflorus, with an IC50 of 2 microg/ml.     

Chemical composition and antimicrobial activity of the essential oils of the Amazon Guatteriopsis species

The essential oils of Guatteriopsis blepharophylla, Guatteriopsis friesiana and Guatteriopsis hispida were obtained by hydrodistillation and analysed by GC and GC/MS. The main compound found in the leaf oil of G. blepharophylla was caryophyllene oxide (1) (69.25%). The leaf oil of G. friesiana contained predominantly beta-eudesmol (2) (51.60%), gamma-eudesmol (3) (23.70%), and alpha-eudesmol (4) (14.56%). The major constituents identified in the leaf of G. hispida were beta-pinene (38.18%), alpha-pinene (30.77%) and (E)-caryophyllene (20.59%). The antimicrobial activity of the essential oils was evaluated against 11 species of microorganisms. The oil of G. friesiana exhibited significant antimicrobial activity for all microorganisms tested, whereas that of G. hispida and G. blepharophyla had potent activity against Rhodococcus equi with MIC of 50 microg mL(-1). The major constituents of each oil were also tested separately, and showed lower activity compared to the oils. Moreover, mixtures of the main constituents, in the same proportions found in G. friesiana and G. hispida oils, did not show the same activity as the original oils.     

Essential oil composition of Achyrocline flaccida (Weinm.) DC. (Asteraceae) from different locations of Argentina

The qualitative and quantitative composition of the essential oils obtained from the inflorescences of Achyrocline flaccida (Asteraceae) has been investigated for the first time. Plant material was collected from eleven locations in Argentina. The essential oils were obtained by hydrodistillation (0.1–0.8% v/w, dried material) and analyzed by GC–FID–MS. Eighty-three compounds were identified representing more than the 90% of the oils. The major components were α-pinene and β-caryophyllene. Statistical analysis was performed in order to evaluate the variability of the essential oils analyzed. Two groups were formed reflecting only quantitative differences in the content of major compounds. The chemical pattern of essential oils observed for A. flaccida is similar to other Achyrocline species studied, except Achyrocline hyperchlora.     

Enteridinines A and B from slime mold Enteridium lycoperdon

Two novel deoxysugar esters, named enteridinines A and B, were isolated from the slime mold Enteridium lycoperdon. Their structures, including the absolute configurations of the hydroxyl and methyl groups, were determined by means of extensive spectroscopic data such as UV, IR, MS, 1D and 2D NMR spectra. Enteridinines A and B have unique structures containing 1,7-dioxaspiro[5.5]undecanes with an O-beta-D-mycarosyl-(1-->4)-beta-D-olivosyl and an O-beta-L-olivomycosyl-(1-->4)-beta-D-amicetosyl-(1-->4)-beta-L-digitoxosyl unit, respectively, and showed growth inhibitory activities against Gram positive bacteria.     

Champanones, yellow pigments from the seeds of champa (Campomanesia lineatifolia)

Chemical investigation of the methanol extract of the seeds of Campomanesia lineatifolia Ruiz and Pav. (Myrtaceae) led to the isolation of two new beta-triketone type compounds, named champanones A (1) and B (2), together with the known 2,3-dihydro-5-hydroxy-6,8,8-trimethyl-2-phenyl-4H-1-benzopyran-4,7(8H)-dione (champanone C) (3). The structures of 1 and 2 were determined to be 2,2,4,4-tetramethyl-6-(1-oxo-3-phenylprop-2-enyl) cyclohexane-1,3,5-trione (occurs as an enol form) and 2,2,4-trimethyl-6-(1-oxo-3-phenylprop-2-enyl)cyclohexane-1,3,5-trione (occurs as an enol form), respectively, by means of spectroscopic analysis. The three compounds showed mild antimicrobial activity.     

Essential oil composition of nine Apiaceae species from western United States that attract the female Indra Swallowtail butterfly (Papilio indra)

Aletes acaulis, Cymopterus hendersonii, Cymopterus panamintensis var. acutifolius, Lomatium rigidum, Lomatium scabrum var. tripinnatum, Musineon tenuifolium, Sphenosciadium capitellatum, Tauschia arguta and Tauschia parishii are among the twenty-two species of the Apiaceae family to which female Indra Swallowtail butterflies (Papilio indra: Lepidoptera) are attracted for oviposition. Because plant volatile oils are known to be attractants for female butterflies, the percent composition of the essential oils of each species was studied. Amongst the nine host plants 168 essential oil components were identified representing between 84% and 99% of the oils. Principal Components Analysis and hierarchical cluster analysis on the essential oil compositions of the larval host plants against four non-larval host plants separated the hosts from the non-hosts into distinct clusters. Volatile components of the oils common to the nine species of Apiaceae are correlated with the expression of physiological attraction behavior by the butterfly.     

Comparative analysis of volatiles from Drimys brasiliensis Miers and D. angustifolia Miers (Winteraceae) from Southern Brazil

The essential oils obtained from Southern Brazilian native Drimys brasiliensis Miers and Drimys angustifolia Miers were analyzed by GC and GC/MS. The oils from leaves of both species showed predominance of monoterpenoids, while the oils from stem barks were characterized by sesquiterpenoids. Bicyclogermacrene (20.0% in leaves and 25.4% in stem bark) and drimenol (1.4% in leaves and 26.2% in stem bark) were the most abundant in D. angustifolia, and cyclocolorenone (from 16.0% to 32.3% in fresh and dried leaves and almost 50% in stem bark) in D. brasiliensis. The oil from fruits of D. brasiliensis was also analyzed and presented 31.0% of cyclocolorenone. The predominance of this unusual aromadendrane-type sesquiterpene in D. brasiliensis essential oils could be used as a chemosystematic marker.     

Vibrational spectroscopic studies to acquire a quality control method of Eucalyptus essential oils

This article presents a novel and original approach to analyze in situ the main components of Eucalyptus oil by means of Raman spectroscopy. The obtained two-dimensional Raman maps demonstrate a unique possibility to study the essential oil distribution in the intact plant tissue. Additionally, Fourier Transform (FT)-Raman and attenuated total reflection (ATR)-IR spectra of essential oils isolated from several Eucalyptus species by hydrodistillation are presented. Density Functional Theory (DFT) calculations were performed in order to interpret the spectra of the essential oils of the Eucalyptus species. It is shown that the main components of the essential oils can be recognized by both vibrational spectroscopic techniques using the spectral information of the pure terpenoids. Spectroscopic analysis is based on the key bands of the individual volatile substances and therefore allows one to discriminate different essential oil profiles of several Eucalyptus species. It has been found that the presented spectroscopic data correlate very well with those obtained by gas chromatography (GC) analysis. All these investigations are helpful tools to generate a fast and easy method to control the quality of the essential oils with vibrational spectroscopic techniques in combination with DFT calculations.     

In vitro antifungal, anti-elastase and anti-keratinase activity of essential oils of Cinnamomum-, Syzygium- and Cymbopogon-species against Aspergillus fumigatus and Trichophyton rubrum

This study was aimed to evaluate effects of certain essential oils namely Cinnamomum verum, Syzygium aromaticum, Cymbopogon citratus, Cymbopogon martini and their major components cinnamaldehyde, eugenol, citral and geraniol respectively, on growth, hyphal ultrastructure and virulence factors of Aspergillus fumigatus and Trichophyton rubrum. The antifungal activity of essential oils and their major constituents was in the order of cinnamaldehyde>eugenol>geraniol=C. verum>citral>S. aromaticum>C. citratus>C. martini, both in liquid and solid media against T. rubrum and A. fumigatus. Based on promising antifungal activity of eugenol and cinnamaldehyde, these oils were further tested for their inhibitory activity against ungerminated and germinated conidia in test fungi. Cinnamaldehyde was found to be more active than eugenol. To assess the possible mode of action of cinnamaldehyde, electron microscopic studies were conducted. The observations revealed multiple sites of action of cinnamaldehyde mainly on cell membranes and endomembranous structures of the fungal cell. Further, test oils were also tested for their anti-virulence activity. More than 70% reduction in elastase activity was recorded in A. fumigatus by the oils of C. verum, C. martini, eugenol, cinnamaldehyde and geraniol. Similar reduction in keratinase activity in A. niger was recorded for the oils of C. martini and geraniol. Maximum reduction (96.56%) in elastase activity was produced by cinnamaldehyde whereas; geraniol caused maximum inhibition (97.31%) of keratinase activity. Our findings highlight anti-elastase and anti-keratinase activity of above mentioned essential oils as a novel property to be exploited in controlling invasive and superficial mycoses.     

竹枝细柄草花序挥发油成分的GC-MS分析

采用常压水蒸气蒸馏法提取竹枝细柄草(Capillipedium assimile (Steud.)A.Camus)花序的挥发油,经GC-MS分析,从花序挥发油中鉴定出45种化合物,占总油量的93.24%.其中含量较高的为4-十一烷酮(18.520%)、(E)-己酸-2-己烯酯(8.042%)、4-壬醇(7.778%)、...