The inflorescence and leaf essential oils of Tanacetum vulgare L. var. vulgare growing wild in Lithuania

Forty samples of inflorescences and leaves of wild Tanacetum vulgare L. var. vulgare were collected in 20 habitats from Lithuania. The essential oils were analyzed by GC and GC/MS. The 57 identified compounds in the oils made up 80.7–99.6%. According to the cluster analysis the volatile oils were divided into four groups with 1,8-cineole (23.6–46.3%, 11 oils), trans-thujone (35.7–78.4%, 6 samples), camphor (19.8–61.8%, 17 oils) and myrtenol (13.1–24.9%, 6 samples) as main constituents. The inflorescences and leaves of tansy plants formed the oils with the same dominating constituent in 15 of the 20 habitats investigated. The leaves in five localities produced oils of the 1,8-cineole chemotype, while the inflorescences biosynthesized oils of the camphor type in three habitats and of the myrtenol type in two habitats. Amounts of the 1,8-cineole in all leaf oils were greater than that in inflorescence oils of the plants from the same locality. An opposite correlation was determined for camphor, myrtenol, cis- and trans-thujone. The myrtenol chemotype was not noticed earlier in the essential oils of T. vulgare.     

Chemical composition and antimicrobial activity of essential oils from Scabiosa arenaria Forssk: growing wild in Tunisia

The essential oils isolated from three organs, i.e., fruits, stems and leaves, and flowers, of the endemic North African plant Scabiosa arenaria Forssk. were screened for their chemical composition, as well as their possible antibacterial, anticandidal, and antifungal properties. According to the GC-FID and GC/MS analyses, 61 (99.26% of the total oil composition), 79 (98.43%), and 51 compounds (99.9%) were identified in the three oils, respectively. While α-thujone (34.39%), camphor (17.48%), and β-thujone (15.29%) constituted the major compounds of the fruit oil, chrysanthenone (23.43%), together with camphor (12.98%) and α-thujone (10.7%), were the main constituents of the stem and leaf oil. In the case of the flower oil, also chrysanthenone (38.52%), camphor (11.75%), and α-thujone (9.5%) were identified as the major compounds. Furthermore, the isolated oils were tested against 16 Gram-positive and Gram-negative bacteria, four Candida species, and nine phytopathogenic fungal strains. It was found that the oils exhibited interesting antibacterial and anticandidal activities, comparable to those of thymol, which was used as positive control, but no activity against the phytopathogenic fungal strains was observed.     

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.     

Assessment of the essential oil composition of Tornabenea annua, Tornabenea insularis and Tornabenea tenuissima fruits from Cape Verde Islands

The essential oils of Tornabenea annua, Tornabenea insularis and Tornabenea tenuissima herbarium or in vivo fruits, collected in Fogo, Santiago, Santo Antão, São Nicolau and São Vicente Islands, from Cape Verde archipelago, or from plants grown in Lisbon, Portugal, were isolated by hydrodistillation and analysed by GC and GC–MS. The yellowish oils were obtained in variable average yields, lower in herbarium samples [0.05% (v/w)] and higher from in vivo samples [1.3% (v/w)]. Whereas T. annua fruits' oils were all dominated by myristicin (92–100%), most of the T. insularis fruit samples' oils were elemicin rich (82–90%). No clear information could be obtained for T. tenuissima fruits' oils as each of the samples gave different chemical composition. Cluster analysis of the essential oil composition from the fruits' samples studied, confirmed these chemical differences.     

Distribution and essential oils of Salvia pomifera subsp. pomifera (Labiatae) on the island of Crete (S Greece)

The distribution of Salvia pomifera subsp. pomifera (Cretan sage) on the island of Crete is presented. The essential oils of six populations scattered on the island are studied. The essential oil content varies from 2.1–4.2%, whereas the main oil components were in all cases α- and/or β-thujone (27.4–72.3% and 7.1–40.8%, respectively). The comparison of our results to literature data, suggest that S. pomifera can be distinguished from S. fruticosa (Greek sage), on the basis of its essential oil composition.     

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.     

Genetic resources of Tunisian Artemisia arborescens L. (Asteraceae), pattern of volatile metabolites concentration and bioactivity and implication for conservation

Artemisia arborescens L. (Asteraceae) is an endemic and a valuable medicinal and ornamental species in the Mediterranean regions. Despite the interest given to A. arborescens L. as promising medicinal crop, this species is becoming threatened of extinction in Tunisia as a result of the fragmentation of its habitat and the absence of any specific measures for its conservation and valorisation. Based on the last considerations, extent information about their volatile metabolites profiling, contents and antimicrobial potential were undertaken based on fourteen populations originated from various geographical and bioclimatic habitats of Tunisia. The obtained results reveal an essential oil content mean value of 1.47%. The leaves of Tunisian tree wormwood populations were dominated by camphor (15.05–58.05%), chamazulene (11.72–45.26%) and β-thujone (0–36.53%). Based on the three first major compounds detected for each population, four different oil types were defined (Oil type I: camphor-chamazulene-β-thujone; Oil type II: camphor-chamazulene-terpinen-4-ol; Oil type III: camphor-chamazulene-bornyl acetate; Oil type IV: camphor-chamazulene-linalool). PCA, HCA and Heatmap chemometric analyses revealed three classification clusters defined mainly by minor compounds. These minor volatile metabolites succeed to discriminate among the fourteen studied populations which promote their chemotaxonomic interest. Our findings confirm previous reports concerning this species in the world and show chamazulene, camphor and β-thujone as the major compounds of this species which define their well known chemotypes independently of the geographical, bioclimatic and genotypic factors. This makes of these three components promising chemosystematic tool for the discrimination of A. arborescens L. in the genus Artemisia. The results showed that the four tested oils were effective against the nine tested microbial strains. The highest antimicrobial potential was revealed for the population AAr_MB characterized by camphor, chamazulene and β-thujone as the dominant components. The pattern of essential oils concentration offers wide range of possibilities for the initiation of breeding programs according to the desired bioactive compounds. Both in situ and ex situ conservation strategies were suggested for the maintenance of the highest chemical polymorphism of this valuable medicinal species.     

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.     

Biodegradation of pyridine raffinate by two bacterial co-cultures of Bacillus cereus (DQ435020) and Alcaligenes faecalis (DQ435021)

This study deals with the optimization of bacterial degradation of pyridine raffinate by previously isolated two aerobic bacteria ITRCEM1 (Bacillus cereus) and ITRCEM2 (Alcaligens faecalis) with accession number DQ4335020 and DQ435021, respectively. The degradation of pyridine raffinate was studied by axenic and mixed bacterial consortium at different nutritional and environmental conditions after the removal of formaldehyde from pyridine raffinate (FPPR). Results revealed that the optimum degradation of pyridine raffinate was observed by mixed bacterial culture in presence of glucose (1% w/v) and peptone (0.2% w/v) at 20% FPPR, pH 7.0, temperature 30°C and 120 rpm at 168 h incubation period . The HPLC analysis of degraded pyridine raffinate samples has indicated the complete removal of α, β and γ picoline. Further, the GC–MS analysis of FPPR pyridine raffinate has shown the presence of pyrazine acetonitrile (6.74), 1,3-dioxepin (8.68), 2-pyridine carboxaldehyde (11.26), propiolactone (12.06), 2-butanol (13.10), benzenesulfonic acid (16.22) and 1,4-dimethyl pyperadine while phenol (17.64) and 3,4-dimethyl benzaldehyde as metabolic products of FPPR.     

Production of (R)-3-hydroxybutyric acid by fermentation and bioconversion processes with Azohydromonas lata

Feasibility of producing (R)-3-hydroxybutyric acid ((R)-3-HB) using wild type Azohydromonas lata and its mutants (derived by UV mutation) was investigated. A. lata mutant (M5) produced 780 mg/l in the culture broth when sucrose was used as the carbon source. M5 was further studied in terms of its specificity with various bioconversion substrates for production of (R)-3-HB. (R)-3-HB concentration produced in the culture broth by M5 mutant was 2.7-fold higher than that of the wild type strain when sucrose (3% w/v) and (R,S)-1,3-butanediol (3% v/v) were used as carbon source and bioconversion substrate, respectively. Bioconversion of resting cells (M5) with glucose (1% v/w), ethylacetoacetate (2% v/v), and (R,S)-1,3-butanediol (3% v/v), resulted in (R)-3-HB concentrations of 6.5 g/l, 7.3 g/l and 8.7 g/l, respectively.     

Variation of Salvia fruticosa Essential Oils on the Island of Crete (Greece)

The essential oil content and composition of Salvia fruticosa (Greek sage) plants growing wild in 20 localities scattered on the island of Crete are studied. The results of our analyses have shown a noticeable variation in the essential oil content (ranging from 1.1 up to 5.1 %) and the amount of the four main oil components: 1,8-cineole (22.7 ? 64.2% of total oil), α-thujone (1.0 ? 19.2%) β-thujone (0.9 ? 25.6%) and camphor (0.8 ? 30.3%). Discriminant analysis revealed that the variation pattern of the essential oil content and the amount of the four main oil components is geographically related, following a W → E direction. Plants grown in Western Crete show a lower essential oil content and their oils are characterised by the predominance of 1,8-cineole. On the other hand, those collected from Eastern Crete exhibit higher values in essential oil content and their oils, besides 1,8-cineole, are rich in α- and β-thujone or camphor. Our findings are further discussed in relation to literature data.     

Acaricidal Activity of Pla.nt Essential Oils against Tyrophagus putrescentiae (Acari: Acaridae)

The acaricidal activity of 54 commercially available plant essential oils against Tyrophagus putrescentiae adults was compared with those of benzyl benzoate and N, N-diethyl-m-toluamide (deet). Responses varied with test oils. In a test with an impregnated fabric disc bioassay at 12.7 μg/cm², over 80% mortality was observed with bay, citronella java, clove bud, clove leaf, lemongrass, nutmeg, oregano, pimento berry, thyme red, and thyme white oils. These oils were more toxic to T. putrescentiae adults than benzyl benzoate and deet. At 6.4 μg/cm², lemongrass and thyme white oils exhibited 76 and 84% mortality, respectively, whereas the acaricidal activity of the other essential oils was significantly decreased. In a fumigation test with adult mites, lemongrass and pimento berry oils were much more effective in closed containers than in open ones, indicating that the effects of these oils were largely due to action in the vapor phase. Plant essential oils described merit further study as potential T. putrescentiae control agents.     

Stability of CoQ10-Loaded Oil-in-Water (O/W) Emulsion: Effect of Carrier Oil and Emulsifier Type

Co-enzyme Q10 (CoQ10), a lipophilic compound that widely used in the food and pharmaceutical products was formulated in a κ-carrageenan coated oil-in-water (O/W) emulsion. In this work, we examined the solubility of CoQ10 in different carrier oils and effects of emulsifier type on the formation and stability of CoQ10-loaded O/W emulsion. Nine vegetable oils and four types of emulsifiers were used. CoQ10 was found significantly (p?<?0.05) more soluble in medium chain oils (coconut oil and palm kernel oil) as compared to other vegetable oils. The O/W emulsions were then prepared with 10 % (w/w) coconut oil and palm kernel oil containing 200 g CoQ10/L oil stabilized by 1 % (w/v) emulsifiers (sucrose laurate (SEL), sodium stearoyl lactate (SSL), polyglycerol ester (PE), or Tween 80 (Tw 80)) in 1 % (w/v) κ-carrageenan aqueous solution. Particle size distribution and physical stability of the emulsions were monitored. The droplet sizes (surface weighted mean diameter, D[3,2]) of fresh O/W emulsion in the range of 2.79 to 5.83 μm were observed. Irrespective of the oil used, results indicated that complexes of SSL/κ-carrageenan provided the most stable CoQ10-loaded O/W emulsion with smaller and narrower particle size distribution. Both macroscopic and microscopic observations showed that O/W emulsion stabilized by SSL/κ-carrageenan is the only emulsion that exhibited no sign of coalescence, flocculation, and phase separation throughout the storage period observed.     

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.     

Hairy root cultures of Anethum graveolens (dill): establishment, growth, time-course study of their essential oil and its comparison with parent plant oils

Transformed root cultures of Anethum graveolens were induced by inoculation of aseptically grown seedlings with Agrobacterium rhizogenes carrying plasmid pRi 1855. The main component of the essential oils from the fruits and from the roots of the parent plant was carvone, whereas -phellandrene and apiole were dominant in the oil from, respectively, the aerial parts and the hairy roots. The essential oils from the fruits, aerial parts and roots of the parent plant were at 2%, 0.3% and 0.06% (v/w), respectively, but only 0.02% (v/w) in the hairy root cultures. Growth of the hairy root cultures reached 600 mg dry wt/50 ml medium after 50 days. The essential oil composition did not change significantly during their growth.     

1,8-cineole and castor oil in sodium lauryl ether sulphate disrupt reproduction and ovarian tissue of Rhipicephalus (Boophilus) microplus

Essential and fixed oils have been researched as alternatives to chemical acaricides. The activity of volatile compounds from essential oils (1,8-cineole, citral and eugenol) at 1.0% (w/v) and fixed oil (castor oil) at 0.3% (w/v) dissolved in 2.0% (v/v) dimethyl sulfoxide (DMSO) + 0.2% (w/v) Tween 80^® was assessed against Rhipicephalus microplus using immersion tests. 1,8-cineole (29.0%) and castor oil (30.2%) had the highest reproductive inhibition rate. A second experiment was performed to verify the effect of the 1,8-cineole (10.0% w/v) and, or castor oil (0.3% w/v) on tick reproduction using different solubilizing agents. The highest reproductive inhibition was observed for the combination of 1,8-cineole/castor oil (94.1%) and 1,8-cineole in 2.0% (w/v) sodium lauryl ether sulphate (SLES) (92.8%). A third experiment showed morphological changes in R. microplus oocytes at different stages of development, as well as in pedicel cells. The most intense effects were observed when ticks were immersed in the formulation containing 1,8-cineole (10.0% w/v) and castor oil (0.3% w/v) dissolved in 2% (w/v) SLES. These findings highlight the potential of this formulation as an alternative for managing cattle ticks as their cytotoxic effects can reduce R. microplus reproductive success.     

Chemical Composition of the Essential Oil and Diethyl Ether Extract of Trinia glauca (L.) Dumort. (Apiaceae) and the Chemotaxonomic Significance of 5‐O‐Methylvisamminol

Analyses by GC, GC/MS, and NMR spectroscopy (1D‐ and 2D‐experiments) of the essential oil and Et₂O extract of Trinia glauca (L .) Dumort . (Apiaceae) aerial parts allowed a successful identification of 220 constituents, in total. The major identified compounds of the essential oil were (Z)‐falcarinol (10.6%), bicyclogermacrene (8.0%), germacrene D (7.4%), δ‐cadinene (4.3%), and β‐caryophyllene (3.2%), whereas (Z)‐falcarinol (47.2%), nonacosane (7.4%), and 5‐O‐methylvisamminol (4.0%) were the dominant constituents of the extract of T. glauca. One significant difference between the compositions of the herein and the previously analyzed T. glauca essential oils (only two reports) was noted. (Z)‐Falcarinol was the major constituent in our case, whereas germacrene D (14.4 and 19.6%) was the major component of the previously studied oils. Possible explanations for this discrepancy were discussed. 5‐O‐Methylvisamminol, a (furo)chromone identified in the extract of T. glauca, has a limited occurrence in the plant kingdom and is a possible excellent chemotaxonomic marker (family and/or subfamily level) for Apiaceae.     

Composition of essential oils from turkish Salvia species

The chemical composition of the essential oils from five Salvia species from Turkey was determined by GC. The species were S. candidissima, S. cryptantha, S. fruticosa, S. officinalis and S. tomentosa. 24, 22, 20, 19, and 22 components were identified, respectively, the major ones being β-pinene (candidissima), borneol (cryptantha), 1,8-cineole (fruticosa), camphor (officinalis) and β-pinene (tomentosa). α-Pinene in candidissima, camphor in cryptantha, α-thujone in officinalis and 1,8-cineole in tomentosa were the other important components.     

Spatial and developmental expression of key genes of terpene biosynthesis in Tanacetum parthenium

Feverfew (Tanacetum parthenium) is a medicinal plant belonging to the Asteraceae family. To improve understanding terpene metabolism in feverfew, the relative gene expression of four key genes coding 3-hydroxy-3-methylglutarylcoenzyme A reductase (HMGR) and germacrene A synthase (GAS) from the mevalonic acid pathway (MVA), as well as 1-deoxy-D-xylulose-5-phosphate reductoisomerase (DXR) and hydroxy-2-methyl-2-(E)-butenyl-4-diphosphate reductase (HDR) from the methyl erythritol phosphate pathway (MEP), were examined. Target organs and tissues included young leaves (not fully expanded), mature leaves (fully expanded), flowers, stems, roots, and glandular trichomes. HMGR, DXR, and HDR were isolated and sequenced for the first time in feverfew. Real-time quantitative PCR analysis revealed differential expression of these genes in feverfew tissues and developmental stages.