Chemical Composition of Essential Oils and Local Knowledge of Myrica gale in Lithuania.

Myrica gale L. (Myricaceae) is an essential oil-bearing plant that is rare in Lithuania and naturally grows only in the western part of the country. The aim of this study was to analyze the composition of essential oils of Myrica gale in different habitats in Lithuania and in different parts of the plant, as well as evaluate the local knowledge about M. gale as a medicinal and aromatic plant. Samples of fruits and leaves (from one and three M. gale populations, respectively) were studied separately. Essential oils were isolated from dried fruits and leaves by hydrodistillation and analyzed by GC/FID and GC/MS methods. Results showed that M. gale fruits accumulated 4.03 ± 2.13% essential oils, meanwhile leaves-up to 19 times less. A total of 85 compounds were identified in the essential oils of the M. gale. Monoterpene hydrocarbons accounted for about half of the total essential oil content; meanwhile, either monoterpene hydrocarbons or sesquiterpene hydrocarbons (depending on habitat) dominated in leaves. The main compounds (depending on habitat) in essential oils of fruits and leaves were α-pinene, 1,8-cineole, limonene, δ-cadinene, and (E)-nerolidol. The high variation in the composition of M. gale essential oils suggests the presence of different chemotypes within the studied habitats of this plant. Evaluation of local knowledge of M. gale through the survey of 74 residents of 15 villages in western Lithuania showed that only 7% of respondents knew this plant. Poor knowledge of M. gale could be related to the narrow range of the natural species' distribution in Lithuania.

Vertical Columns with Sustainable Green Cover: Meadow Plants in Urban Design.

Unique vertical column structures were constructed for the greening of a structure at the Botanical Garden of Vilnius University, in which a plant cover was formed using the turf rolls of semi-natural meadows that were wrapped on 197 columns, with each column consisting of three equal segments. By evaluating the species composition and the abundance of vegetation in the segments of the columns, we studied how this natural cover changes and what its survival potential is. During the five years of observation, 97 plant species were determined in total. Over time, the initial plant species of fertile soils were mostly replaced by ruderal, nitrophilous, and pioneer plants. Out of the 58 original species, 18 disappeared, while 39 new ones emerged. In the vegetation cover on the north exposition of the building, the original species composition declined faster. The most persistent species were ruderal short-lived Conyza canadensis, Melilotus albus, and Urtica dioica, and long-lived Elytrigia repens. As for vegetation classes, the initial plant communities of the Molinio-Arrhenatheretea elatioris vegetation class were partially replaced by the plant communities of the Koelerio-Corynephoretea canescentis and Artemisietea vulgaris classes; however, unformed plant communities finally became prevalent. All directions, including the north, east, south and west, were equally dominated by semi-shade- and semi-light-loving plant species, together with a less abundant representation of light-loving species. Meanwhile, an unexpected establishment of the light-loving annual Arabidopsis arenosa was observed on the least illuminated north exposition. Likewise, the perennial Festuca pratensis, which is particularly resistant to wintering, emerged and spread on all expositions. The vegetation in the vertical columns was dynamic, and the initial plant species significantly diminished in the five years; however, as new species took place, the columns remained sufficiently covered with a green carpet of plants. This study reveals the benefits of using semi-natural meadow turfs in vertical greening of buildings in the harsh climate of a 5b hardiness zone, which is accompanied by distressing climatic fluctuations during the vegetation season.

Variations in Yield, Essential Oil, and Salicylates of Filipendula ulmaria Inflorescences at Different Blooming Stages.

Meadowsweet (Filipendula ulmaria) is an essential oil-bearing, pharmacologically valuable medicinal plant growing wild in floodlands that are either not usually used for agriculture or have low economic value. The aim of this work was to understand the relationship between the yield of F. ulmaria inflorescences and the qualitative and quantitative composition of the essential oil during flowering stages in different habitats. Five different habitats of F. ulmaria were investigated for evaluation of inflorescence characteristics (length and weight) and the quantitative and qualitative composition of essential oils in early and late blooming stages (growing stage BBCH 62−63 and BBCH 65−67/72−73, respectively). The results showed significant (p < 0.05) positive correlations between the length and weight of inflorescences both in early and in late blooming stages (r = 0.73 and r = 0.72, respectively). The early blooming stage was observed to have 1.2−2 times greater quantity of volatile oils in comparison with the late blooming stage. Salicylaldehyde and methylsalicylate were the main salicylates in both blooming stages. Spearman's correlation showed statistically significant relationship between percentages of salicylaldehyde and methylsalicylate (r = −0.94, p < 0.05). An increase in salicylaldehyde was accompanied by a decrease in methylsalicylate in essential oils. Statistically significant relations between the investigated parameters of plant and the parameters of habitat were not detected. The dried raw material yield of F. ulmaria in 1 ha in the late blooming stage was 18−56% higher than in the early blooming stage; however, the yield of essential oil in the early flowering stage was 1.5−1.6 times higher than in the late flowering stage. The obtained research data suggest that the low economic value of floodlands­the habitats of F. ulmaria­can be increased by using these areas as natural industrial plots.

Impact of Edaphic and Climatic Factors on Thymus pulegioides Essential Oil Composition and Potential Prevalence of Chemotypes.

Intraspecific chemical polymorphism is characteristic of essential oil bearing Thymus pulegioides (Lamiaceae). Soil chemical composition and climatic conditions can influence not only quantitative and qualitative composition of essential oils, but also on prevalence of different chemotypes in space. The purpose of study was to determine the impact of edaphic and climatic factors on T. pulegioides essential oil composition and potential chemotypes prevalence. It were investigated 131 habitats of T. pulegioides in all ten climatic sub-districts of Lithuania. Essential oils were isolated by hydrodistillation and analysed by GC-FID and GC-MS. The content of humus was estimated by oxidation method, the content of mobile potassium (K2O) and mobile phosphorus (P2O5)-flame photometry using 0.2 M HCl solution, the soil pH-electrometrically and 15 elements of soil-by energy-dispersive X-ray fluorescence. The meteorological data (temperature, rainfall, photosynthetically active solar radiation and sunshine duration) were obtained from the meteorological bulletins. Results showed that humus in soil positively, manganese and cobalt-negatively influenced on the essential oil accumulation in T. pulegioides. Carvacrol was the most common compound in the essential oil of T. pulegioides; higher amounts of sulphur and mobile phosphorus, lower amounts of sodium in soil, higher rainfall in blooming period are favourable for this compound and for potential prevalence of carvacrol chemotype. Geraniol was frequent in the eastern and the central part of Lithuania, where the temperature in vegetation season is higher, and in soils characterised by higher and lower amounts of sodium and chlorine, respectively. Thymol, linalool and α-terpinyl acetate were rare. Edaphic and climatic conditions can differently influence on essential oil yield and chemical composition of species as well as on potential prevalence of different chemotypes of same species in space.

Geraniol and Carvacrol in Essential Oil Bearing Thymus pulegioides: Distribution in Natural Habitats and Phytotoxic Effect.

Phenolic and non-phenolic chemotypes of Thymus pulegioides L. are common in Europe. Essential oils of these chemotypes, as various compositions of allelochemicals, can have different phytotoxic effects on neighboring plants in natural habitats. The aim of this study was to establish the distribution of carvacrol and geraniol in T. pulegioides, growing wild in Lithuania, and compare phytotoxity of essential oils of carvacrol and geraniol chemotypes on selected plant species. In investigating 131 T. pulegioides habitats, essential oils were isolated by hydrodistillation and analyzed by GC-FID and GC-MS. Phytotoxity of essential oils extracted from carvacrol and geraniol chemotypes transmitted through water and air to selected plants was determined under laboratory conditions. Pharmacologically valuable Hypericum perforatum L. and the important forage grass Phleum pratense L. were respectively selected for experimentation from among 35 medicinal plants and 10 feed Poaceae species, growing in T. pulegioides habitats. Field results showed that carvacrol is common throughout Lithuania's territory, whereas the geraniol is predominantly located under the continental climatic conditions of the eastern region of the country. In the laboratory experiment, it was established that there was stronger inhibition of P. pratense seed germination by the essential oil of the geraniol chemotype than the carvacrol chemotype. None of the H. perforatum seeds germinated after exposure to the essential oil of the geraniol chemotype. In general, this study builds on previous studies by providing further evidence that different T. pulegioides chemotypes have contrasting phytotoxic effects on neighboring plants within their natural habitats.

Dynamics of Isomeric and Enantiomeric Fractions of Pinene in Essential Oil of Picea abies Annual Needles during Growing Season.

Norway spruce (Picea abies (L.) H. Karst.) is one of the most important commercial tree species distributed naturally in the Boreal and subalpine forest zone of Europe. All parts of spruce trees, including needles, accumulate essential oils with a variety of chemical properties and ecological functions, such as modulating plant-insect communication. Annual needle samples from 15 trees (five from each of three habitats) of 15-17 years old were assayed for essential oils and their major compounds, including α-pinene, ß-pinene, (1S)-(-)-α-pinene, and (1R)-(+)-α-pinene across a growing season. Results showed strong positive correlation between percentages of α- and ß-pinene isomers (r = 0.69, p < 0.05) and between pinene isomers and essential oils: α-pinene correlated with essential oil stronger (r = 0.62, p < 0.05) than ß-pinene (r = 0.33, p < 0.05). Correlation analyses performed with some weather conditions, including average monthly temperature, growing sum of effective temperatures over 5 °C, duration of sunshine, accumulated precipitation, relative humidity, and pressure, showed that temperature is the most important weather condition related to pinene dynamics: negative correlations of moderate strength were established between percentages of α- and ß- pinenes and average monthly temperatures (r = -0.36, p < 0.01, n = 75 and r = -0.33, p < 0.01, n = 75, respectively). Out of pinene enantiomers, only (1S)-(-)-α-pinene showed some negative correlation with monthly temperature (r = -0.26, p < 0.05, n = 75). Different patterns of essential oil and pinene dynamics during growing season within separate habitats suggested that some genetic variables of Picea abies might be involved.

α-Terpinyl Acetate: Occurrence in Essential Oils Bearing Thymus pulegioides, Phytotoxicity, and Antimicrobial Effects.

The aim of this study was to evaluate occurrence of T. pulegioides α-terpinyl acetate chemotype, as source of natural origin α-terpinyl acetate, to determine its phytotoxic and antimicrobial features. Were investigated 131 T. pulegioides habitats. Essential oils were isolated by hydrodistillation and analyzed by GC-FID and GC-MS. Phytotoxic effect of essential oil of this chemotype on monocotyledons and dicotyledons through water and air was carried out in laboratory conditions; the broth microdilution method was used to screen essential oil effect against human pathogenic microorganisms. Results showed that α-terpinyl acetate was very rare compound in essential oil of T. pulegioides: it was found only in 35% of investigated T. pulegioides habitats. α-Terpinyl acetate (in essential oil and pure) demonstrated different behavior on investigated plants. Phytotoxic effect of α-terpinyl acetate was stronger on investigated monocotyledons than on dicotyledons. α-Terpinyl acetate essential oil inhibited seeds germination and radicles growth for high economic productivity forage grass monocotyledon Poa pratensis, but stimulated seed germination for high economic productive forage legume dicotyledon Trifolium pretense. α-Terpinyl acetate essential oil showed high antimicrobial effect against fungi and dermatophytes but lower effect against bacteria and Candida yeasts. Therefore, T. pulegioides α-terpinyl acetate chemotype could be a potential compound for developing preventive measures or/and drugs for mycosis.

Composition of essential oil of lemon thyme (Thymus × citriodorus) at different hydrodistillation times.

Distillation time can both to optimise the production and to engineer the composition of essential oil in essential oil bearing plants. Purpose of this study was to evaluate the effect of duration of hydrodistillation on composition of essential oil of Thymus × citriodorus, the natural source of commercially important geraniol and citral, a component with valuable biological properties. Essential oils were isolated by hydrodistillation at different distillation times and analysed by GC/MS analytical methods. Increase in percentage of essential oil during all hydrodistillation time gradient was uneven. Elongation of hydrodistillation time decreased percentages of monoterpenes but increased percentages of sesquiterpenes in essential oil. Results showed that the hydrodistillation of essential oil from lemon thyme longer than 60 min is useless.

Influence of plant origin natural α-pinene with different enantiomeric composition on bacteria, yeasts and fungi.

Although the nature-identical chemical compounds are cheaper, they not always repeat biological activity of plant origin natural chemical compounds, often react allergies and resistance of microorganisms. The aim of this study was to investigate effects of Juniperus communis origin α-pinene with different enantiomeric composition on bacteria, yeasts and fungi. Results showed that different enantiomeric composition of α-pinene have different activities on microorganisms: essential oil with (1S)-(-) ≈ (1R)-(+) enantiomeric composition of α-pinene influenced on some microorganisms stronger than essential oil with (1S)-(-) < (1R)-(+) enantiomeric composition of α-pinene; the pure natural α-pinene with enantiomeric composition S < R more strongly inhibited growth of investigated bacteria and Candida yeasts, α-pinene with enantiomeric composition S ≈ R - growth of Trichophyton and Aspergillus. (1S)-(-) and (1R)-(+) enantiomeric forms of α-pinene can have also different synergistic effects with other compounds of essential oil. The results of study showed that the same amount of α-pinene with different enantiomeric composition can have diverse antimicrobial potential due different specific interactions with other chemical compounds of essential oil. Therefore, it is very important to determine and present the enantiomeric composition of those plant origin compounds, which are characterized by enantiomerisation, during the course of research of biological activities of natural plant products (essential oils and other) and their isolated compounds.

Antifungal properties of hypericin, hypericin tetrasulphonic acid and fagopyrin on pathogenic fungi and spoilage yeasts.

CONTEXT: The role of hypericin-mediated photodynamic antimicrobial properties on pathogenic fungi and photodynamic therapy for human cancer cells is known. Antifungal properties of Hypericum perforatum L. (Hypericaceae) and Fagopyrum esculentum Moench. (Polygonaceae) extracts were also studied. The different polarities of solvents can cause complication in the identification of antifungal effects of separate biologically active compounds. In recent experimental work, we compared antifungal properties of purified hypericin, hypericin tetrasulphonic acid (hypericin + S) and fagopyrin, which is analogue of hypericin. OBJECTIVE: The antifungal properties of aromatic polyketide derivatives such as hypericin, hypericin + S and fagopyrin on the selected pathogenic fungi and spoilage yeasts have been studied. MATERIALS AND METHODS: The antifungal properties of hypericin, hypericin + S and fagopyrin were determined using the broth microdilution method against a set of pathogenic fungi and spoilage yeasts including: Microsporum canis, Trichophyton rubrum, Fusarium oxysporum, Exophiala dermatitidis, Candida albicans, Kluyveromyces marxianus, Pichia fermentans and Saccharomyces cerevisiae. The tested concentrations of hypericin, hypericin + S and fagopyrin ranged from 750 to 0.011 µg/mL and MIC values were evaluated after 48 h incubation at 30 °C. RESULTS: The results confirm different antifungal properties of hypericin, hypericin + S and fagopyrin on the selected pathogenic fungi and spoilage yeasts. For pathogenic fungi, the minimum inhibitory concentrations of hypericin ranged 0.18-46.9 µg/mL, hypericin + S 0.18-750 µg/mL and fagopyrin 11.7-46.9 µg/mL. For spoilage yeasts, the MICs of hypericin and hypericin + S ranged 0.18-46.9 and 0.011-0.73 µg/mL, respectively. DISCUSSION AND CONCLUSION: The results obtained herein indicate that various chemical structures of hypericin, hypericin + S and fagopyrin can develop different antifungal properties.

Effects of meteorological conditions and plant growth stage on the accumulation of carvacrol and its precursors in Thymus pulegioides.

The effects of meteorological conditions (temperature, rainfall, photosynthetically active solar radiation (PAR) and sunshine duration) and plant growth stages on the quantitative composition of a secondary metabolite - essential oil and its main compounds, in the carvacrol chemotype of Thymus pulegioides L. (Lamiaceae) cultivated in open ground were studied under the same micro-edaphoclimatic environmental conditions for six years. The essential oil was isolated by hydrodistillation, the analysis of monoterpenic phenol carvacrol and the biogenetic precursors (monoterpene hydrocarbons p-cymene and γ-terpinene) were carried out annually using GC-FID and GC-MS. In the carvacrol chemotype investigated in this study, the yield of essential oil varied from 0.72% to 0.98% (CV = 12%) at full flowering stage. Regression analysis showed a significant negative relationship between the amount of essential oil and both temperature and rainfall during T. pulegioides flowering (July) and the period from April (beginning of vegetation) to July, but a strong positive relationship with photosynthetically active solar radiation during April-July (beta = 0.658, p < 0.05). The percentage of carvacrol, p-cymene and γ-terpinene ranged between 16.88 and 29.29% (CV = 18%), 5.54-11.33% (CV = 23%) and 20.60-24.43% (CV = 6%) respectively. Regression analysis showed the significant positive relationship between the percentage of carvacrol and sunshine duration at the flowering stage (in July) (beta = 0.699, p < 0.05); while the negative relationship was established between the percentages of precursors of carvacrol and photosynthetically active solar radiation and sunshine duration. The accumulation of p-cymene, the percentage of which varied most strongly from all investigated chemical compounds, showed significant positive relationships with temperature and rainfall during the period April-July and temperature in July (beta = 0.617, beta = 0.439 and beta = 0.429 respectively, p < 0.05). The analysis of plant growth stages showed that the highest amount of essential oil in carvacrol chemotype of T. pulegioides accumulated at ripening/seed maturity stage. The percentage of carvacrol increased gradually from the stem elongation to the post-flowering/seed maturity stage, overtaking the full flowering stage by 22%. The highest carvacrol content in the T. pulegioides carvacrol chemotype coincided with the highest oil yield during the fruiting stage. The amount of essential oil was also measured at the second full flowering stage, because after cutting the aerial part of the plant at the full flowering stage T. pulegioides often bloom for a second time: the carvacrol chemotype accumulated by 21% lower yield of essential oil at this stage compared to the first flowering, however, only traces of carvacrol and its precursors were found at the second full flowering stage.

Hastifolins A-G, antifeedant neo-clerodane diterpenoids from Scutellaria hastifolia.

From the aerial parts of Scutellaria hastifolia, family Lamiaceae (Labiatae), seven neo-clerodane diterpenoids (hastifolins A-G) were isolated. The products are similar to the known scuteparvin and are characterized by being trans-cinnamoyl derivatives. Structures and stereochemistry were determined by intensive NMR investigation. Six of the products form three pairs of epimers at C-13. Hastifolins A-C showed significant antifeedant activity.