Search

Euphorbia seguieriana ssp. seguieriana Necker (ES) and Euphorbia cyparissias (EC) with a habitat in the Deliblato Sands were the subject of this examination. The latexes of these so far insufficiently investigated species of the Euphorbia genus are used in traditional medicine for the treatment of wounds and warts on the skin. To determine their chemical composition, non-targeted screening of the latexes’ chloroform extracts was performed using liquid chromatography coupled with quadrupole time-of-flight mass spectrometry employing an electrospray ionization source (LC-ESI QTOF MS). The analysis of the obtained results showed that the latexes of ES and EC represent rich sources of diterpenes, tentatively identified as jatrophanes, ingenanes, tiglianes, myrsinanes, premyrsinanes, and others. Examination of the anticancer activity of the ES and EC latex extracts showed that both extracts significantly inhibited the growth of the non-small cell lung carcinoma NCI-H460 and glioblastoma U87 cell lines as well as of their corresponding multi-drug resistant (MDR) cell lines, NCI-H460/R and U87-TxR. The obtained results also revealed that the ES and EC extracts inhibited the function of P-glycoprotein (P-gp) in MDR cancer cells, whose overexpression is one of the main mechanisms underlying MDR.

Chemotaxonomy presents various challenges that need to be overcome in order to obtain valid and reliable results. Individual genetic and environmental variations can give a false picture and lead to wrong conclusions. Applying a holistic approach, based on multivariate data analysis, these challenges can be overcome. Thus, a metabolomics approach has to be optimized depending on the subject of research. We used 1H NMR-based metabolomics as a potential chemotaxonomic tool on the selected Euphorbia species growing wild in Serbia. Principal components analysis (PCA), soft independent modeling by class analogy (SIMCA) and Orthogonal Projections to Latent Structures Discriminant Analysis (OPLS-DA) were used to analyze obtained NMR data in order to reveal chemotaxonomic biomarkers. The standard protocol for plant metabolomics was optimized aiming to extract more specific metabolites, which are characteristic for the Euphorbia genus. The obtained models were validated, which revealed that variables unique for each species were associated with certain classes of molecules according to literature data. In E. salicifolia, acacetin-7-O-glycoside (not found before in the species) was detected, and the structure of the aglycone part was solved based on 2D NMR data. In the presented paper, we have shown that metabolomics can be successfully used in Euphorbia chemotaxonomy.

The chemical composition of the essential oil of fresh young needles with twigs of Douglas fir (Pseudosuga menziesii Mirb. Franco) obtained by hydrodistillation were analyzed by gas chromatography (GC) and gas chromatography–mass spectrometry (GC–MS). Ten compounds, accounting for 94.26 % of the oil, were identified. The main compounds found were bornyl acetate (34.65 %), camphene (29.82 %), a-pinene (11.65 %) and santene (5.45 %). The antifungal activity of the essential oil was tested against various fungal species. The minimum inhibitory concentration of Douglas fir essential oil ranged from 1.5 to 4 µg mL-1. The fungi most sensitive to the tested oil were Phomopsis helianthi, while Penicillium species, along with Microsporum canis, were the most resistant. Compared to the commercial fungicidal agent bifonazole, the studied essential oil demonstrated higher antifungal activity.

Resveratrol, which occurs in two isomeric forms, trans and cis, is a phytoalexin with numerous pharmacological activities, such as anti-cancer, antiviral, neuroprotective and anti-aging. Red wine is the main source of the compound and an easy way of including resveratrol in the human diet. In this study, the most popular commercial Serbian wines (red, white and rosé-type) were analyzed for their content of trans- and cis-resveratrol. The analysis was performed by HPLC with a UV detector. Prior to the injection, phenolic compounds were extracted onto a LiChrolut RP18 bonded silica cartridge. The concentration of trans-resveratrol ranged from 0.11 to 1.69 mg L-1 and cis-resveratrol from 0.12 to 1.49 mg L-1.

Rutin (1, main constituent) and two flavone C-glycosides, vitexin (2) and vitexin 2''-O-alpha-rhamnopyranoside (3) were isolated from the aerial parts of Onobrychis montana subsp. scardica. They were identified by 1H-NMR, 13C-NMR and UV–Vis spectroscopy (procedure with shift reagents), and high resolution ESI-MS. A relatively high content of 1 (5.27 mg/g of dry plant material), measured by HPLC, indicated O. montana subsp. scardica as a new natural source of this biologically active compound. The isolated flavonoid compounds might be of value as chemotaxonomic markers.

The investigation of roots of Anthemis cotula (Asteraceae) from east Serbia revealed, in addition to polyacetylenes previously isolated from the same species, three prenylated 4-hydroxyacetophenosnes, detected for the first time in any Anthemis species. It is possible that they act as phytoalexins in the plant. From the aerial parts, six linear sesquiterpene lactones (four known and two new ones), as well as two known flavones, apigenin and hispiduli, wee isolated.

The conformations of the C-6 lactonized germacranolides 13 were calculated by applying the PM3 semi-empirical method. The low-temperature 1H-NMR spectra of parthenolide (1) were also measured. The relations between the calculated and the experimentally determined geometries were established using a modified Karplus equation. The applied quantum-chemical calculations proved to be an efficient and easy-to-use tool for the elucidation and prediction of the properties of germacranolide-type sesquiterpene lactones.

1. Introduction 2. Results 3. Asteraceae 3.1. Genus Artemisia L. 3.1.1. Artemisia annua L. 3.1.2. Artemisia vulgaris L. 3.1.3. Artemisia absinthium L. (warmwood) 3.1.4. Artemisia scoparia W. et K. 3.1.5. Artemisia camprestris L. 3.2. Genus Ambrosia L. 3.2.1. Ambrosia artemisiifolia L. (the common rag weed) 3.3. Genus Tanacetum L. (syn. Chrysanthemum L.) 3.3.1. Tanacetum parthenium L. (feverfew) 3.3.2. Tanacetum serotinum L. 3.3.3. Tanacetum vulgare L. (tansy) 3.3.4. Tanacetum macrophyllum Willd. 3.3.5. Tanacetum corymbosum L. 3.4. Genus Telekia Baumg. 3.4.1. Telekia speciosa (Schreb.) Baumg. 3.5. Genus Inula L. 3.5.1. Inula helenium L. 3.5.2. Inula spiraeifolia L. 3.6. Genus Eupatorium L. 3.6.1. Eupatorium cannabinum L. 3.7. Genus Achillea L. 3.7.1. Achillea abrotanoides Vis. 3.7.2. Achillea millefolium subsp. pannonica 3.7.3. Achillea crithmifolia W. et K. 3.7.4. Achillea clypeolata Sibth. et Sm. 3.7.5. Achillea serbica Nyman 3.7.6. Achillea depressa Janka 3.8. Genus Anthemis L. 3.8.1. Anthemis carpatica Willd. 3.8.2. Anthemis cretica L. subsp. cretica 3.9. Genus Centaurea L. 3.9.1. Centaurea derventana Vis. et Panc. 3.9.2. Centaurea kosaninii Hayek 3.9.3. Centaurea solstitialis L. 4. Apiaceae 4.1. Genus Laserpitium L. 4.1.1. Laserpitium siler L. 4.1.2. Laserpitium marginatum L. 4.1.3. Laserpitium latifolium L. 4.1.4. Laserpitium alpinum W. K. 4.2. Genus Angelica L. 4.2.1. Angelica silvestris L. 4.3. Genus Peucedanum L. 4.3.1. Peucedanum austriacum (Jacq.) Koch

Seed extracts from eight grape cultivars (Vitis vinifera) growing in Serbia were screened for their polyphenolic composition by means of HPLC/PDA/ESI/MS analysis. The study revealed 34 phenolic compounds belonging to the following groups: flavan-3-ol monomers, proanthocyanidins, flavonols, hydroxycinnamic acid and hydroxybenzoic acid derivatives. The quantities of the main constituents were determined using PDA/HPLC. Qualitative and quantitative differences among the cultivars were observed.

In this study, volatile compounds were analyzed in five samples of home-made spirit beverage made by the distillation of fermented fruits of cornelian cherry (Cornus mas L.). The major volatile compounds, besides ethanol, identified and quantified were: methanol, acetaldehyde, 1-propanol, ethyl acetate, 2-methyl-1-propanol, 1-butanol, amyl alcohols, 1-hexanol and 2-phenylethanol. The minor volatiles were submitted to liquid–liquid extraction with dichloromethane and analyzed by gas chromatography and gas chromatography/ /mass spectrometry (GC/MS). A total of 84 compounds were identified. The most abundant compounds were straight-chain free fatty acids, ethyl esters of C6–C18 acids, limonene, 2-phenylethanol and 4-ethylphenol. Most of the compounds found in the “Drenja” spirits investigated in this study are similar to those present in other alcoholic beverages.

4-Chlorobenzoic acid (1), quercitrin (2), astilbin (3), along with β-sitosterol, γ-sitosterol, friedelin and β-amyrin were isolated from the aerial parts of Hypericum monogynum. Whereas compound 1 was isolated for the first time from natural sources, flavanonol 3 was not found before in these species.

1H-NMR spectroscopy was applied for the quantitative analysis of cnicin, a bioactive germacranolide type sesquiterpene lactone, in the aerial parts of seven wild-growing Centaurea species collected in Serbia and Montenegro. The analysis was performed by comparison of the integral of the one-proton signal of cnicin (H-13, δ 5.75) with that of the two-proton singlet (δ 6.98) of 2,6-bis(1,1-dimethylethyl)-4-methylphenol (BHT), used as the internal standard. Cnicin, within concentration the range 1.06–6.12 mg/g, calculated per weight of the fresh plant material was detected in six species, the exception being C. salonitana. This method allows the rapid and simple quantification of cnicin without any pre-purification step.

Essential oils from leaves with young branches of Cotinus coggygria Scop. from two localities in Serbia (Deliblatska pescara and Zemun), obtained by hydrodistillation, were analysed by GC–MS. Thirty-one component were identified from both oils and among them monoterpenic hydrocarbons were the dominant class (87.4 and 93.1 %). The dominant constituent in both essential oils was limonene (47.0 and 39.2 %). Both oils were also tested for antibacterial and antifungal activities. In comparison to streptomycin, both oils showed slightly higher activity (against most Gram-positive bacteria) in the disc diffusion method and slightly lower activity when the microdilution method was employed. They also exhibited antifungal potential higher than that of the commercial fungicide bifonazole.

Two flavonoid glycosides 1 and 2 having the luteolin structure were isolated from flowers of the endemic plant species Cephalaria pastricensis. They were identified by 1H and 13C NMR, as well as UV/Vis spectroscopy. The structures of 1 and 2 were also confirmed by the spectral data of aglycones and TLC of the sugars obtained after acid hydrolysis. Flavones 1 and 2 showed significant antiradical activity in the 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay.

Five tetrahydrofuran sesquiterpenes, so-called davanones, and coumarin umbelliferone isolated from Artemisia lobelii All. var. canescens (DC.) Briqu, were tested for antifungal activity. All the compounds inhibited the growth of the applied fungi. The overall activity of one of them, 2-hydroxy-2,6,10-trimethyl-7,10-epoxydodeca- 3,11-dien-5-on, was comparable to that of the antibiotic bifonazole.

Five lignans with a 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane skeleton, epieudesmin, kobusin, pinoresinol, fargesin and sesartemin, were isolated from the aerial parts and roots of Achillea lingulata. Their structures were identified by comparison of their 1H-NMR and MS data to those in the literature. Fargesin and pinoresinol have not been isolated previously from any species of the genus Achillea.

A 29-year-old Para 2 was admitted to the emergency department with increasing lower abdominal pain. The patient had undergone an uncomplicated elective repeat caesarean section 7 days before being admitted to the emergency department. An emergency laparotomy revealed a uterus didelphys with a torsion of one of the uteri.