Phytochemical Variability of Essential Oils of Two Balkan Endemic Species: Satureja pilosa Velen. and S. kitaibelii Wierzb. ex Heuff. (Lamiaceae).

Satureja pilosa and S. kitaibelii (Lamiaceae) are Balkan endemic plant species, and the composition of their essential oil (EO) is highly variable. The aim of the present study was to establish: (1) the EO variability in two populations of S. pilosa (the intrapopulation), and (2) the EO variation in S. kitaibelii between nine populations (interpopulation) from Bulgaria and two from Serbia. The EOs of two Satureja species were obtained from aboveground plant parts by hydrodistillation and were analyzed by GC/MS/FID. Overall, the EO yield on the intrapopulation level of S. pilosa varied from 0.54% to 2.15%, while the EO of S. kitaibelii varied from 0.04% to 0.43% (interpopulation). The EO of S. pilosa was found to contain thymol and carvacrol as the main constituents, with other major constituents being p-cymene and γ-terpinene. S. pilosa samples in both studied populations formed six chemical groups. The major constituents (p-cymene, terpinen-4-ol, bornyl acetate, γ-muurolene, endo-borneol, cis-ß-ocimene, trans-ß-ocimene, carvacrol, α-pinene, thymoquinone, geranial, geranyl acetate, spathulenol, and caryophyllene oxide) of S. kitaibelii EO were considered for grouping the populations into ten chemotypes. The present study is the first report on the interpopulation diversity of S. kitaibelii EOs in Bulgaria. It demonstrated variability of the EOs between and within the populations of S. kitaibelii from Bulgaria. This study identified promising genetic material that could be further propagated and developed into cultivars for commercial production of S. kitaibelii and S. pilosa, thereby reducing the impact of collection on wild populations.

Juniperus horizontalis Moench: Chemical Composition, Herbicidal and Insecticidal Activities of Its Essential Oil and of Its Main Component, Sabinene.

The composition, herbicidal, larvicidal, and toxic activities of Juniperus horizontalis Moench essential oil and sabinene, its main component, were evaluated. The seed germination percentage and root length of eight different plant species (crops and weeds) were measured for in vitro herbicidal activity tests. Different doses (100, 50, 10, 5, 1, 0.5 µg/mL) of the samples were applied to seeds for 120 h. The same doses were applied to test the toxicity of the samples on Tubifex tubifex (sludge worm) and Chironomus aprilinus (blood worm). Four doses (435, 652.5, 870, and 1740) of samples were in a larvicidal test on Tenebrio molitor L. (mealworm), and bioassays were checked after 24 and 48 h. The analysis of the oil allowed for the identification of dominant components as sabinene (38.7%), α-pinene (10.0%), elemol (8.6%), γ-terpinene (8.3%), limonene (7.8%) and α-thujene (5.3%). The results showed that the effect of oil on root length inhibition was significant in all crop species. The doses which affected root growth were not toxic to Tubifex tubifex and Chironomus aprilinus. Finally, the obtained results in the larvicidal bioassay indicate that the potential of J. horizontalis in yellow mealworm survivorship limitation can be a starting point for future research.

Green extraction of hemp (Cannabis sativa L.) using microwave method for recovery of three valuable fractions (essential oil, phenolic compounds and cannabinoids): a central composite design optimization study.

BACKGROUND: Solvent-free microwave-assisted extraction (MAE) is a green extraction method capable of boosting the yield and quality profile of hemp essential oil when compared with other conventional extraction techniques. During this process, two by-products are produced, namely the aqueous residue containing bioactive phenolics and the residual deterpenated biomass, which can be used for further extraction and purification of phytocannabinoids. To date, the hemp industry has not utilized these products, although they can be valuable for the food, cosmetic, nutraceutical and pharmaceutical market. RESULTS: This study assessed and optimized the variables affecting MAE efficiency, namely microwave irradiation power, extraction time and added water, which were studied using a central composite design approach, and results were used to optimize the extraction process for recovering three valuable fractions: essential oil, polyphenols and phytocannabinoids. The products obtained using the optimized conditions were characterized in terms of yield, chemical profile and antioxidant potential. Moreover, the by-products obtained during the optimized run were further analyzed in terms of their biological activity using both enzymatic and non-enzymatic assays. The aqueous residue demonstrated a powerful α-glucosidase inhibition, a good activity in terms of superoxide radical scavenging activity, a modest efficacy in terms of inhibition of advanced glycation end products formation and no activity in terms of lipase inhibition. The residual deterpenated biomass did not possess significant biological activity. CONCLUSION: This work demonstrated valorization of industrial hemp essential oil and its by-products, obtained by a sustainable and eco-friendly extraction method, through an almost waste-free approach. Cannabinoids as well as other valuable bioactive compounds such as glycosidic flavones may be recovered from the residues of the essential oil extraction, representing interesting substances in the pharmaceutical, cosmetic and nutraceutical fields. © 2022 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.

Biological Activity of Essential Oils of Four Juniper Species and Their Potential as Biopesticides.

The objective of this study was to assess the biological activity of essential oils (EOs) of four Juniperus species obtained via two different distillation methods and their potential as biopesticides. The studied factors were juniper species (Juniperus communis L., J. oxycedrus L., J. pygmaea C. Koch., and J. sibirica Burgsd), plant sex (male (M) and female (F)), and distillation method (hydrodistillation via a standard Clevenger apparatus (ClevA) and semi-commercial (SCom) steam distillation). The hypothesis was that the EO will have differential antioxidant, antimicrobial, and insecticidal activities as a function of plant species, plant sex, and distillation method. The two distillation methods resulted in similar EO composition within a given species. However, there were differences in the EO content (yield) due to the sex of the plant, and also differences in the proportions of some EO components. The concentration of α-pinene, ß-caryophyllene, δ-cadinene and δ-cadinol was dissimilar between the EO of M and F plants within all four species. Additionally, M and F plants of J. pygmaea, and J. sibirica had significantly different concentrations of sabinene within the respective species. The EOs obtained via ClevA extraction showed higher antioxidant capacity within a species compared with those from SCom extraction. All of the tested EOs had significant repellent and insecticidal activity against the two aphid species Rhopalosiphum padi (bird cherry-oat aphid) and Sitobion avenae (English grain aphid) at concentrations of the EO in the solution of 1%, 2.5%, and 5%. The tested EOs demonstrated moderate activity against selected pathogens Fusarium spp., Botrytis cinerea, Colletotrichum spp., Rhizoctonia solani and Cylindrocarpon pauciseptatum. The results demonstrate that the standard ClevA would provide comparable EO content and composition in comparison with SCom steam distillation; however, even slight differences in the EO composition may translate into differential bioactivity.

Essential Oil Composition and Bioactivity of Two Juniper Species from Bulgaria and Slovakia.

Juniperus excelsa M. Bieb and J. sabina L. contain essential oil (EO), while J. sabina also contains podophyllotoxin, which is used as a precursor for anti-cancer drugs. Two studies were conducted. The first assessed the variability in the EO profile and podophyllotoxin concentration of the two junipers, depending on the location and tree gender. The main EO constituents of J. excelsa were α-cedrol, α-limonene and α-pinene, while the constituents in J. sabina were sabinene, terpinen-4-ol, myrtenyl acetate and α-cadinol. The podophyllotoxin yield of 18 J. sabina accessions was 0.07-0.32% (w/w), but this was not found in any of the J. excelsa accessions. The second study assessed the effect of hydrodistillation (Clevenger apparatus) and steam distillation (in a semi-commercial apparatus) on the EO profile and bioactivity. The extraction type did not significantly alter the EO composition. The EO profiles of the two junipers and their accessions were different and may be of interest to the industry utilizing juniper leaf EO. Breeding and selection programs could be developed with the two junipers (protected species) in order to identify chemotypes with (1) a high EO content and desirable composition, and (2) a high concentration of podophyllotoxin in J. sabina. Such chemotypes could be established as agricultural crops for the commercial production of podophyllotoxin and EO.

Grinding and Fractionation during Distillation Alter Hemp Essential Oil Profile and Its Antimicrobial Activity.

The hypothesis of this study was that we can modify the essential oil (EO) profile of hemp (Cannabis sativa L.) and obtain fractions with differential composition and antimicrobial activity. Therefore, the objective was to evaluate the effects of grinding of hemp biomass before EO extraction and fractionation during distillation on EO profile and antimicrobial activity. The study generated a several EO fractions with a diversity of chemical profile and antimicrobial activity. The highest concentrations of ß-pinene and myrcene in the EO can be obtained in the 5-10 min distillation time (DT) of ground material or in the 80-120 min DT of nonground material. High δ-3-carene and limonene EO can be obtained from 0-5 min DT fraction of nonground material. High eucalyptol EO can be sampled either in the 0-5 min DT of the ground material or in the 80-120 min of nonground material. Overall, the highest concentrations of ß-caryophyllene, α-(E)-bergamotene, (Z)-ß-farnesene, α-humulene, caryophyllenyl alcohol, germacrene D-4-ol, spathulenol, caryophyllene oxide, humulene epoxide 2, ß-bisabolol, α-bisabolol, sesquiterpenes, and cannabidiol (CBD) can be obtained when EO is sampled in the 80-120 min DT and the material is nonground. Monoterpenes in the hemp EO can be increased twofold to 85% by grinding the material prior to distillation and collecting the EO in the first 10 min. However, grinding resulted in a slight but significant decrease in the CBD concentration of the EO. CBD-rich oil can be produced by collecting at 120-180 min DT. Different EO fractions had differential antimicrobial activity. The highest antimicrobial activity of EO fraction was found against Staphylococcus aureus subsp. aureus. THC-free EO can be obtained if the EO distillation is limited to 120 min. The results can be utilized by the hemp processing industry and by companies developing new hemp EO-infused products, including perfumery, cosmetics, dietary supplements, food, and pharmaceutical industries.

Industrial Hemp (Cannabis sativa subsp. sativa) as an Emerging Source for Value-Added Functional Food Ingredients and Nutraceuticals.

Industrial hemp (Cannabis sativa L., Cannabaceae) is an ancient cultivated plant originating from Central Asia and historically has been a multi-use crop valued for its fiber, food, and medicinal uses. Various oriental and Asian cultures kept records of its production and numerous uses. Due to the similarities between industrial hemp (fiber and grain) and the narcotic/medical type of Cannabis, the production of industrial hemp was prohibited in most countries, wiping out centuries of learning and genetic resources. In the past two decades, most countries have legalized industrial hemp production, prompting a significant amount of research on the health benefits of hemp and hemp products. Current research is yet to verify the various health claims of the numerous commercially available hemp products. Hence, this review aims to compile recent advances in the science of industrial hemp, with respect to its use as value-added functional food ingredients/nutraceuticals and health benefits, while also highlighting gaps in our current knowledge and avenues of future research on this high-value multi-use plant for the global food chain.

Chemical Characterization and Antibacterial Activity of Essential Oil of Medicinal Plants from Eastern Serbia.

The objective of this study was to evaluate wild growing Satureja kitaibelii, Thymus serpyllum, Origanum vulgare, Achillea millefolium and Achillea clypeolata with respect to their essential oil (EO) content, composition and antimicrobial activity. The five species were collected at Mt. Rtanj and the village of Sesalac, Eastern Serbia. The main EO constituents of Lamiaceae plants were p-cymene (24.4%), geraniol (63.4%) and germacrene D (21.5%) in Satureja kitaibelii, Thymus serpyllum and Origanum vulgare ssp. vulgare, respectively. A. millefolium EO had multiple constituents with major ones being camphor (9.8%), caryophyllene oxide (6.5%), terpinen-4-ol (6.3%) and 1,8-cineole (5.6%), while the main EO constituents of A. clypeolata were 1,8-cineole (45.1%) and camphor (18.2%). Antimicrobial testing of the EO showed that Staphylococcus aureus (Gram-positive) was more sensitive to all of the tested EOs than Escherichia coli (Gram-negative). S. kitaibelii EO showed the highest antimicrobial activity against both tested bacterial strains. This is the first study to characterize the EO composition and antimicrobial activity of these five medicinal species from Eastern Serbia in comparison with comprehensive literature data. The results can be utilized by the perfumery, cosmetics, food and pharmaceutical industries, but also for healing purposes in self-medication.

Industrial, CBD, and Wild Hemp: How Different Are Their Essential Oil Profile and Antimicrobial Activity?

Hemp (Cannabis sativa L.) is currently one of the most controversial and promising crops. This study compared nine wild hemp (C. sativa spp. spontanea V.) accessions with 13 registered cultivars, eight breeding lines, and one cannabidiol (CBD) hemp strain belonging to C. sativa L. The first three groups had similar main essential oil (EO) constituents, but in different concentrations; the CBD hemp had a different EO profile. The concentration of the four major constituents in the industrial hemp lines and wild hemp accessions varied as follows: ß-caryophyllene 11-22% and 15.4-29.6%; α-humulene 4.4-7.6% and 5.3-11.9%; caryophyllene oxide 8.6-13.7% and 0.2-31.2%; and humulene epoxide 2, 2.3-5.6% and 1.2-9.5%, respectively. The concentration of CBD in the EO of wild hemp varied from 6.9 to 52.4% of the total oil while CBD in the EO of the registered cultivars varied from 7.1 to 25%; CBD in the EO of the breeding lines and in the CBD strain varied from 6.4 to 25% and 7.4 to 8.8%, respectively. The concentrations of δ9-tetrahydrocannabinol (THC) in the EO of the three groups of hemp were significantly different, with the highest concentration being 3.5%. The EO of wild hemp had greater antimicrobial activity compared with the EO of registered cultivars. This is the first report to show that significant amounts of CBD could be accumulated in the EO of wild and registered cultivars of hemp following hydro-distillation. The amount of CBD in the EO can be greater than that in the EO of the USA strain used for commercial production of CBD. Furthermore, this is among the first reports that show greater antimicrobial activity of the EO of wild hemp vs. the EO of registered cultivars. The results suggest that wild hemp may offer an excellent opportunity for future breeding and the selection of cultivars with a desirable composition of the EO and possibly CBD-rich EO production.

Essential Oil Yield and Composition of the Balkan Endemic Satureja pilosa Velen. (Lamiaceae).

Satureja pilosa Velen. senso lato is a Balkan endemic plant that is not well characterized and is found on rocky outcrops of limestone base in Stara Planina (the Balkan Mountains) and the Rhodope Mountains. The objective of this study was to assess the variability of essential oil (EO) content and composition of S. pilosa collected at 33 locations across the Balkan and Rhodope Mountains in Bulgaria using advanced statistical methods including cluster analysis. The EO content in dried aboveground biomass varied from 0.52% to 2.03%. More than 21 EO constituents were identified, belonging to the groups of monoterpenes and sesquiterpenes. The monoterpenes were the predominant class, comprising 84.8% to 96.1% of the total EO. Thymol and carvacrol were the major constituents of the phenolic monoterpenoids. Thymol varied from 36.6% to 67.1% and carvacrol varied from 52.4% to 93.0% of the total oil. p-Cymene also varied widely, from 9.6%-34.0%. There were significant variations between locations and within a location in the EO content and composition. This study identified several chemotypes: (1) thymol and p-cymene; (2) thymol, p-cymene and γ-terpinene; (3) carvacrol and p-cymene; (4) carvacrol, p-cymene and γ-terpinene; and (5) carvacrol. This is the first comprehensive study on the endemic plant S. pilosa that identified several chemotypes based on the EO composition. The S. pilosa EO from the five different chemotypes exhibited larvicidal and mosquito repellent activity against Aedes aegypti. The identified chemotypes can be utilized for the development of new varieties with desirable compositions to meet specific industry needs and new mosquito management control products.

GC-MS Composition and Olfactory Profile of Concretes from the Flowers of Four Nicotiana Species.

The genus Nicotiana (Solanaceae) includes over 70 species, with a long history of traditional use; many of them are nowadays used in bioengineering, biosynthesis, molecular biology, and other studies, while common tobacco, N. tabacum L., is one of the most economically important industrial crops worldwide. Although Nicotiana species have been extensively investigated, relatively less research has focused on flowers, especially research related to obtaining aromatic products for cosmetic and perfumery use. On the other hand, there is evidence that Nicotiana flowers accumulate various secondary metabolites with a distinct aroma and biological activities, and the flowers represent a biomass available in sufficient quantities. Therefore, this study aimed to determinate the chemical composition (by GC-MS) and the olfactory profiles of a specific type of natural aromatic product (concrete), obtained from the flowers of four Nicotiana species, in a direct comparison between them. The yields of extracted concrete were sufficiently high, varying between the species, 1.4% (N. rustica L.), 2.5% (N. glutinosa L.), 1.6% (N. alata Link&Otto genotype with white flowers), 2.7% (N. alata genotype with pink flowers), 3.2% (N. tabacum, Oriental type), and 5.2% (N. tabacum, Virginia type). The major components of the obtained concretes belonged to different chemical classes: N. rustica and N. tabacum (OR), the hydrocarbons n-tetratriacontane (14.5%; 15.0%) and n-triacontane (12.1%; 13.3%), and 3-methyl-pentanoic acid (11.1%; 12.2%); N. glutinosa, the diterpenes sclareol (25.9%), 3-α-hydroxy-manool (16.3%), and 13-epimanool (14.9%); N. alata (WF), the phenylpropanoid terephthalic acid and di(2-ethylhexyl) ester (42.9%); N. alata (PF), the diterpene tributyl acetylcitrate (30.7%); and N. tabacum (FCV), the hydrocarbons n-hexacosane (12.9%) and n-pentacosane (12.9%). Each of the flower concretes revealed a characteristic odor profile. This is the first report about Nicotiana species as a source for obtaining flower concretes; these initial results about the concrete yield, olfactory profile, and chemical composition are a prerequisite for the possible processing of Nicotiana flowers into new aromatic products for use in perfumery and cosmetics. The study provides new data in favor of the potential of the four Nicotiana species as aromatic plants, as well as a possible alternative use of flowers, a valuable, but discarded, plant material in other applications.

Utilization of Nutmeg (Myristica fragrans Houtt.) Seed Hydrodistillation Time to Produce Essential Oil Fractions with Varied Compositions and Pharmacological Effects.

The intent of this study was to utilize distillation timeframes (DT) of nutmeg (Myristica fragrans) essential oil (EO) to generate fractions with differential chemical compositions and bioactivity. Ten fractions were captured at the following distillation timeframes: 0.0-0.5, 0.5-1.0, 1.0-2.5, 2.5-5.0, 5.0-10, 10-30, 30-60, 60-90, 90-120, and 120-240 min. In addition, a control EO was collected from a straight 0-240 min non-stop distillation. ANOVA and advanced regression modeling revealed that the produced EO fractions possess substantial variation in the concentration of potentially desired compounds. The concentrations (%) of α-phellandrene, 3-carene, p-cymene, limonene, α-thujene, α-pinene, camphene, sabinene, ß-pinene, and myrcene decreased, while the concentrations (%) of α-terpinene, γ-terpinene, terpinolene, and myristicin increased in later DT fractions. Nutmeg EO showed some antimalarial activity against Plasmodium falciparum D6, but did not exhibit significant antifungal activity. In general, nutmeg seed oil yields increased with an increase of DT. These results may be utilized by industries using nutmeg EO.

Characterization of Odor-Active Compounds, Polyphenols, and Fatty Acids in Coffee Silverskin.

For the first time the volatile fraction of coffee silverskin has been studied focusing on odor-active compounds detected by gas chromatography-olfactometry/flame ionization detector (GC-O/FID) system. Two approaches, namely headspace (HS) analysis by solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS) and odor-active compounds analysis by gas chromatography-olfactometry/flame ionization detector (GC-O/FID), have been employed to fully characterize the aroma profile of this by-product. This work also provided an entire characterization of the bioactive compounds present in coffee silverskin, including alkaloids, chlorogenic acids, phenolic acids, flavonoids, and secoiridoids, by using different extraction procedures and high performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) system. Coffee silverskin was shown to be a good source of caffeine and chlorogenic acids but also of phenolic acids and flavonoids. In addition, the fatty acid composition of the coffee silverskin was established by GC-FID system. The results from this research could contribute to the development of innovative applications and reuses of coffee silverskin, an interesting resource with a high potential to be tapped by the food and nutraceutical sector, and possibly also in the cosmetics and perfumery.

Chemical Composition of the Essential Oil of the Endemic Species Micromeria frivaldszkyana (Degen) Velen.

Micromeria frivaldszkyana is an endemic species found only in Bulgaria. Its essential oil (EO) composition is unknown. This study assessed the EO yield and composition of M. frivaldszkyana as a function of the location and of drying prior to the EO extraction. M. frivaldszkyana was sampled from two natural habitats, Uzana and Shipka in the Balkan Mountains; the EO was extracted via hydrodistillation and analyzed on GC/MS. The plants from the two locations had distinct EO composition. The EO content (in dried material) was 0.18% (Uzana) and 0.26% (Shipka). Monoterpene ketones were the major group of the EO constituents. Also, hydrocarbons predominated in the EO from Shipka, and alcohols predominated in the EO from Uzana. The EO from Uzana had a greater concentration of menthone (56% vs. 17% from Shipka) and neomenthol (7.8% vs. 2.4%). Conversely, the EO from Shipka had greater concentrations of pulegone (50% vs. 20% from Uzana), limonene (10.1% vs. 2.6%), and germacrene D (3.4% vs. 1.1%). Drying prior to the EO extraction altered the concentration of some constituents. This is the first report of M. frivaldszkyana EO yield and composition. The EO showed some similarities with the chemical profile of other Micromeria species, but overall, it has an unique chemical profile and may have distinctive applications.

Essential Oil Composition of Ruta graveolens L. Fruits and Hyssopus officinalis Subsp. aristatus (Godr.) Nyman Biomass as a Function of Hydrodistillation Time.

The aim of this study was to establish the kinetics regression models for yield and composition of Ruta graveolens fruit and Hyssopus officinalis subsp. aristatus aboveground biomass essential oil (EO), collected at different time intervals during the hydrodistillation process. The hypothesis was that collecting the EO fractions during specific time frames may result in EOs with dissimilar composition that may have differential use by the industry. Furthermore, we calculated the kinetics regression models for the composition of EO, isolated by hydrodistillation in a Clevenger-type apparatus and characterized by GC-MS and GC-FID analyses. The EO yield of R. graveolens fruits was 0.39% (relative area % of GC-FID chromatogram), with major constituents in the Control fraction (0-90 min) being 2-nonanone, 2-undecanone, and 2-undecanol, representing 65% of the total oil. The highest concentration of 2-nonanone (60%) was found in the 30-60 min oil fraction, the concentration of 2-undecanone (35%) was highest in the Control (0-90 min) fraction, and the concentration of eucalyptol (19%) was highest in the 5-10 min fraction. The EO yield of H. officinalis subsp. aristatus dried biomass was 1.12%. The major constituents in the Control fraction (0-90 min) of H. officinalis biomass were eucalyptol, α-pinene, sabinene, ß-pinene, and cis-3-pinanone, representing 86% of the total. Eucalyptol (58%) was the highest in the 0-5 min fraction. The highest ß-pinene (15%) and cis-3-pinanone (20%) contents were found in the 20-40 min fraction. The kinetics regression models that were developed for EO composition of R. graveolens were second-order polynominal, Michaelis-Menten, and Exponential decay, while for EO composition of H. officinalis subsp. aristatus biomass were Exponential decay and Power. The results from this study could benefit the EO industry.

Carotenoid-Related Volatile Compounds of Tobacco (Nicotiana tabacum L.) Essential Oils.

Tobacco (Nicotiana tabacum L.) aroma is an important attribute of tobacco quality and is influenced by a variety of minor chemical components, including carotenoid degradation products. The objectives of this work were to determine the content of the most important fragrance-shaping carotenoid degradation products in the essential oils (EOs) of the three types of Bulgarian tobacco-Oriental (OR), flue-cured Virginia (FCV), and Burley (BU)-and to compare them with other aromatic products from tobacco. The content of total carotenoids and ß-carotene was highest in BU tobacco (22.23 and 20.34 mg/100 g DW, respectively), followed by OR (13.60 and 12.09 mg/100 g DW in variety "Plovdiv 7" (Pd7); 6.27 and 5.45 mg/100 g DW in "Krumovgrad" (Kr), and FCV (5.93 and 3.73 mg/100 g DW). EOs were obtained by hydrodistillation in an acidified medium, and the main aroma-impact compounds from carotenoid degradation (identified by GC-MS) were as follows: FCV-α-ionone (0.61 mg/100 g DW), dihydro-ß-ionone (0.96 mg/100 g DW), ß-damascenone (1.26 mg/100 g DW); BU-α-ionone (0.73 mg/100 g DW), dihydro-ß-ionone (1.19 mg/100 g DW), ß-damascenone (1.35 mg/100 g DW); OR(Kr)-α-ionone (0.20 mg/100 g DW), ß-ionone (1.08 mg/100 g DW), dihydro-ß-ionone (1.34 mg/100 g DW), ß-damascenone (0.36 mg/100 g DW); OR(Pd7)-α-ionone (1.43 mg/100 g DW), dihydro-ß-ionone (1.73 mg/100 g DW), ß-damascenone (1.23 mg/100 g DW). Ionone and its derivatives were not identified in the aroma extraction products concrete, resinoid, or absolute. The results suggest that temperature, pH of the medium, process duration, and possibly other unknown factors affect carotenoid transformation. The study provides insight into the composition of tobacco EOs and may be of interest to the fragrance industry.

Chemical Composition and Antimicrobial Activity of Laurus nobilis L. Essential Oils from Bulgaria.

Laurel, Laurus nobilis L. is an evergreen plant belonging to the Lauraceae family, native to Southern Europe and the Mediterranean area. This is the first report on the composition and bioactivity of laurel essential oil (EO) from Bulgaria. The oil yield was 0.78%, 0.80%, and 3.25% in the fruits, twigs, and leaves, respectively. The main constituents in the fruit EO were 1,8-cineole (33.3%), α-terpinyl acetate (10.3%), α-pinene (11.0%), ß-elemene (7.5%), sabinene (6.3%), ß-phellandrene (5.2%), bornyl acetate (4.4%), and camphene (4.3%); those in the twig EO were 1,8-cineole (48.5%), α-terpinyl acetate (13.1%), methyl eugenol (6.6%), ß-linalool (3.8%), ß-pinene (3.4%), sabinene (3.3%) and terpinene-4-ol (3.3%); and the ones in the leaf EO were 1,8-cineole (41.0%), α-terpinyl acetate (14.4%), sabinene (8.8%), methyl eugenole (6.0%), ß-linalool (4.9%), and α-terpineol (3.1%). The antibacterial and antifungal properties of laurel EOs were examined according to the agar well diffusion method. The leaf EO showed antibacterial and antifungal activities against almost all strains of the microorganisms tested, whereas the twig EO was only able to inhibit Staphylococcus aureus. Pseudomonas aeruginosa ATCC 9027 and Escherichia coli ATCC 8739 were the bacterial strains that showed the highest resistance to the laurel EO. The results can benefit the EO industry and biopesticide development.

Terpenoids in the Essential Oil and Concentrated Aromatic Products Obtained from Nicotiana glutinosa L. Leaves.

N. glutinosa L. is a relatively less studied Nicotiana species (Solanaceae), although there are data about its importance as a model plant in viral control studies, as a gene donor in tobacco hybridization and as a source of agents with insecticidal or fungicidal effects. The biological activities of the species were associated mostly with the presence of leaf surface metabolites, in particular diterpenes and sucrose esters. The aim of this study was to identify the chemical composition of the essential oil (EO) and two aromatic extraction products (concrete and resinoid) obtained from N. glutinosa L. leaves. GC-MS analysis identified 26 components in the EO (representing 97.3% of total oil content), which contained mostly diterpene compounds with major components manool (14.2%), sclarene (8.4%) and manoyl oxide (8.1%). The number of compounds identified in the concrete was 37 (95.5% of the total content) and the major component was the diterpene alcohol sclareol (14.2%). In the resinoid, 30 volatile components (representing 95.1% of resinoid content) were identified, with major components nicotine (32.9%), α-tocopherol (8.2%), tridecanoin (6.9%), sclareol (6.9%), and solanone (6.9%). The group of bicyclic diterpenes had the largest share in the diterpene fraction of the products (57.3%, 91.7%, and 86.3%, respectively for the EO, concrete, and resinoid). Considering the abundance of sclareol in the aromatic products, the antimicrobial activity of the pure substance was determined. Sclareol was highly effective against a set of medicinally important yeasts; Candida albicans АТСС 10231, C. glabrata ATCC 90030, C. parapsilosis clinical isolate, and C. tropicalis NBIMCC 23, while being less effective against the studied Gram-positive and Gram-negative bacteria. Data from the study on N. glutinosa aromatic products composition may be of interest to the aroma industries for their possible use in perfumery and cosmetics.

Coal-Bed Methane Water: Effects on Soil Properties and Camelina Productivity.

Every year, the production of coal-bed natural gas in the Powder River Basin results in the discharge of large amounts of coal-bed methane water (CBMW) in Wyoming; however, no sustainable disposal methods for CBMW are currently available. A greenhouse study was conducted to evaluate the potential to use CBMW as a source of irrigation water for camelina [ (L.) Crantz]. We assessed the effects of three CBMW concentrations (0% [1:0], 50% [1:1], and 100% [0:1] tap water to CBMW) on selected soil properties, growth, seed oil, and fatty acid composition of three camelina cultivars: Blaine Creek, Ligena, and Pronghorn. The 100% CBMW reduced seed and estimated biofuel yields by 24 and 23%, respectively, but increased the oil content by 3%, relative to the control. Additionally, the 100% CBMW visibly affected soil through formation of surface crust due to elevated levels of sodium (653 mg Na kg). The 50% CBMW had no significant effects on the seed yield, estimated biofuel yield, and oil content, but the soil Na levels were still high (464 mg kg), which could pose a long-term impact on soil structure. The CBMW tended to reduce the total saturated fatty acid, but it had no significant effects on the total monounsaturated or polyunsaturated fatty acids of camelina seeds. Overall, CBMW diluted with an equal amount of good-quality water could be used to irrigate camelina in the short term. Afterward, only good-quality water would have to be used until the accumulated dissolved solids are flushed out.

Yield, Composition and Antioxidant Capacity of the Essential Oil of Sweet Basil and Holy Basil as Influenced by Distillation Methods.

The profile and bioactivity of essential oil (EO) depends on genetic, environmental, and other factors. We hypothesized that the basil EO may be influenced by the distillation methods. Hence, a study was conducted to evaluate the effect of steam distillation (SD) and hydrodistillation (HD) extraction method on the yield, composition, and bioactivity of EO of sweet basil (Ocimum basilicum) and holy basil (Ocimum tenuiflorum). In both basil species, the EO yield (content) was significantly higher from SD than from HD. There were significant differences in the compounds' concentrations of EO obtained from SD and HD as well, however, the same compounds were identified in the EO from HD and SD. In the EO of O. basilicum, the concentration of 74% of the identified compounds were higher in SD than HD, whereas in the EO of O. tenuiflorum, the concentration of 84% of identified compounds were higher in SD than in HD. However, the concentrations of two of the major compounds of O. basilicum EO (estragole and methyl cinnamate) and a major compound of O. tenuiflorum EO (methyl eugenol) were significantly higher in HD than in SD. The type of distillation did not affect the antioxidant capacity of basil EO within the species. This study demonstrated that the type of distillation may significantly affect oil yield and composition but not the antioxidant capacity of the EO from sweet and holy basil.