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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.

The presence of n-alkanes, free alcohols and free acids in leaf epicuticular wax extracts of 22 samples of 11 Euphorbia L. species belonging to the sections Paralias, Esula, Myrsiniteae and Helioscopia, 10 of which were never examined before, were analyzed by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS), and n-alkane C27 was detected as the principal component of leaf epicuticular waxes in the majority of the examined species, while the most abundant free alcohol was C26. Three Euphorbia species belonging to section Helioscopia were characterized by a predominance of alcohol C28. Free acid (C16) was the major component in 21 investigated samples. The usefulness of n-alkanes and free alcohols and free acids as potential chemotaxonomic markers is briefly discussed.

Two sets of structurally different jatrophanes (1-11 and 13-16), jatrophane 12, and latex extract of 2 Euphorbia species (17 and 18) were tested for in vitro protective effect against chromosome aberrations in peripheral human lymphocytes using the cytokinesis-block micronucleus (CBMN) assay. Jatrophanes 1-6 in minimal doses of 1 µg/mL prominently decreased micronuclei (MN) frequency in the range 44.86% to 34.29% and manifested considerable protective effect. From the other set of jatrophanes, 13 in the same minimal dose notably decreased MN frequency by 31.05%, while extracts 17 and 18 at a concentration of 4 µg/mL remarkably decreased the frequency of MN by 37.94% and 36.12%, respectively. Jatrophanes 12, 14, and 16 showed moderate protection, while 7-11 and 15 were less active than positive control. The structure-activity relationship (SAR) studies of the tested jatrophanes (1-16) indicated the favorable position of benzoate at C-8 or C-9 (3, 4, and 13) and a preference of isobutanoyloxy group at C-3 (1-3) rather than propanoyloxy at the same position (4-6) for pronounced protective effect on human lymphocytes DNA. In a previous SAR study on 11 jatrophanes (1, 3-8, and 13-16), the same structural features in 3, 4, and 13 influenced powerful inhibition of P-gp, while growth inhibition of cancer cells was more than doubled in 1 (isobutanoyloxy group at C-3) compared to 6 (propanoyloxy at C-3).

Although all ground beetles have pygidial glands homologous in structure and function, there are many differences among species, often significant, in terms of chemical composition of the secretion and morphology of the gland components. In this paper, two predatory ground beetle species of the genus Carabus, namely C. (Tomocarabus) convexus and C. (Procrustes) coriaceus, were subjected to chemical, morphological and histological study of their pygidial glands and the glands' secretions. Altogether, three carboxylic acids were isolated, and the pygidial gland reservoir and other glandular parts are morphologically described in the study. We also tested whether there exist differences in chemical content of the secretion obtained by upsetting the beetles in a traditional way and that obtained directly from intact reservoirs. Detailed data on morphology of the pygidial glands of both species are presented, as well as updated information about the chemical components of the glandular secretions. Apart from tiglic and methacrylic acids, which are typical for Carabus pygidial secretions, we also found benzoic acid as a minor component of the secretion in both species. In addition, a chemotaxonomic overview of Carabus taxa is given in the paper.

In this study, the antibacterial and cytotoxic activities of isolated compounds from the roots of Onosma visianii were investigated. By using different chromatographic techniques and appropriate spectroscopic methods, the seven naphthoquinones were described: deoxyshikonin (1), isobutyrylshikonin (2), alpha-methylbutyrylshikonin (3), acetylshikonin (4), beta-hydroxyisovalerylshikonin (5), 5,8-O-dimethyl isobutyrylshikonin (6) and 5,8-O-dimethyl deoxyshikonin (7). Among the tested compounds, 3 and 4 exhibited the highest antibacterial activities toward all tested bacterial species (MIC50 and MIC90 for gram positive bacteria: 6.40 mu g/mL-12.79 mu g/mL and 6.82 mu g/mL-13.60 mu g/mL, respectively; for gram negative bacteria: 4.27. mu g/mL-8.53 mu g/mL and 4.77 mu g/mL-9.54 mu g/mL, respectively). Also, naphthoquinones 3 and 4 exhibited strong cytotoxic activity against MDA-MB-231 cells (IC50 values 86.0 mu g/mL and 80.2 mu g/mL, respectively), while compounds 1, 3, 4 and 5 significantly decreased viability of HCT116 cells (IC50 values of 97.8 mu g/mL, 15.2 mu g/mL, 24.6 mu g/mL and 30.9 mu g/mL, respectively). Our results indicated that all tested naphthoquinone pigments are potential candidates for clinical uses as antibacterial and cytotoxic agents.

The variations of metabolic profile of the latex of wild-growing Euphorbia palustris was carried out using multivariate analysis of NMR spectral data. One population was infected with fungi Fusarium sporotrichioides, Fusarium proliferatum and Alternaria alternata, while the other consisted of healthy plant species. The non-polar metabolites of latex extracts such as benzoyl ingenol-laurate, amyrin decadienoate esters, cis-1,4-polyisoprene, and 24-methylenecycloartanol were identified using H-1 and 2D NMR spectra. Principal component analysis of H-1 NMR data provided a clear discrimination between the latex of infected and healthy plants. Minimum inhibitory concentration and minimum fungicidal concentration values of the latex extracts of healthy and infected plants were determined. The latex of infected plants was found to contain higher levels of benzoyl ingenol-laurate and 24-methylenecycloartanol, of which concentrations were strongly correlated with the antifungal activities of the latex. (C) 2016 Elsevier Ltd. All rights reserved.

Cuticular hydrocarbons (CHCs) in Drosophila melanogaster represent the basis of chemical communication being involved in many important biological functions. The aim of this study was to characterize chemical composition and variation of cuticular profiles in five D. melanogaster strains. These strains were reared for approximately 300 generations on five diets: standard cornmeal medium and substrates prepared with apple, banana, tomato, and carrot. Differences in quantity and/or quality in CHCs were assumed as a result of activation of different metabolic pathways involved in food digestion and adaptations to the particular diet type. In total, independently of sex and strain, 66 chemical compounds were identified. In females of all strains, 60 compounds were identified, while, in males, 47 compounds were extracted. Certain new chemical compounds for D. melanogaster were found. MANOVA confirmed that CHC amounts significantly depend on sex and substrates, as well as on their interactions. Discriminant analysis revealed that flies belonging to apple' and carrot' strains exhibited the most noticeable differences in CHC repertoires. A non-hydrocarbon pheromone, cis-vaccenyl acetate (cVA) also contributed to the variation in the pheromone bouquet among the strains. Variability detected in CHCs and cVA may be used in the explanation of differences in mating behaviour previously determined in analyzed fly strains.

Differential scanning calorimetry (DSC) technique is used to study the oxidative stability of blackberry (R. fruticosus L., Cacak Thornless cultivar) and raspberry (Rubus idaeus L., Willamette cultivar) seed oils. Oxidative stability of the oil samples was studied in an oxygen atmosphere, isothermally at eight temperatures, T-i (110, 115, 120, 125, 130, 135, 140 and 145 degrees C) and non-isothermally at six heating rates, beta(i) (2, 5, 7.5, 10, 15, 20 degrees C/min). Fatty acid composition was analyzed by gas chromatography (GC MS). High content of essential fatty acids (linoleic and linolenic acid) was detected in both oils. Reaction rate constants (k) and activation energies (E-a) of oil oxidation process were calculated for both isothermal and non-isothermal conditions. Blackberry seed oil was shown to have greater oxidative stability than raspberry seed oil because of a smaller quantity of linolenic fatty acid. (C) 2014 Elsevier B.V. All rights reserved.

Three adult cave-dwelling ground beetle species were induced to discharge secretions of their pygidial glands into vials. Dichloromethane extraction was used to obtain the secretions. In total, 42 compounds were identified by GC/MS analysis. Pheggomisetes ninae contained 32 glandular compounds, Laemostenus (Pristonychus) punctatus 13, whereas Duvalius (Paraduvalius) milutini had nine compounds. Caproic, oleic, palmitic, and stearic acids were present in the samples of all analyzed species. Undecane was predominant in the extract of L. punctatus. Palmitic acid was the major component in the secretion of D. milutini. Finally, the most abundant compounds in P. ninae secretion were heptacosene and nonacosadienes. Herein, we present the first data on the identification of pygidial gland secretion components in both troglophilous and troglobite cave-dwelling ground beetles. Some compounds are reported for the first time in the secretions of ground beetles and other higher or lower taxa. The adaptation to underground life has not led to a reduction or changes in the chemical defense mechanism in the analyzed troglophilous and troglobitic Platyninae and Trechinae taxa.

Tetradenia riparia (Hochstetter) Codd belongs to the Lamiaceae family and it was introduced in Brazil as an exotic ornamental plant. A previous study showed its antimicrobial, acaricidal and analgesic activities. Two compounds were isolated from essential oil of T. riparia leaves and identified as 9 beta, 13 beta-epoxy-7-abietene (1), a new one, and 6,7-dehydroroyleanone (2), already reported for another plant. The structure of these compounds was determined by spectroscopic analysis and by comparison with literature data. The cytotoxic activities of the essential oil and compounds 1 and 2 were determined by a 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) assay, and by tumor cells MDA-MB-435 (human breast carcinoma), HCT-8 (human colon), SF-295 (human nervous system) and HL-60 (human promyelocytic leukemia). The essential oil and compound 1 showed high cytotoxic potential of the cell lines SF-295 (78.06% and 94.80%, respectively), HCT-8 (85.00% and 86.54%, respectively) and MDA-MB-435 (59.48% and 45.43%, respectively). Compound 2 had no cytotoxic activity. The antioxidant activity was determined by 2,2-diphenyl-1-picryl-hydrazyl (DPPH), beta-carotene-linoleic acid system and 2,2'-azinobis-(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) assays. The inhibitory concentration (IC50 in mu g mL(-1)) for essential oil and compound 2 was, respectively 15.63 and 0.01 for DPPH; 130.1 and 109.6 for beta-carotene-linoleic acid and 1524 and 1024 for ABTS. Compound 1 had no antioxidant activity. By fractioning the oil, it was possible to identify two unpublished compounds: 1 with high cytotoxic potential and 2 with high antioxidant potential.

Five yeast strains Saccharomyces cerevisiae and S. bayanus (SB, Top Floral, Top 15, Aroma White and Red Fruit) and two nutrients, diammonium phosphate and Nutriferm Arom, were examined for their influence on young apricot brandies, with a special emphasis on the chemical, volatile and sensory characteristics. Analyses of the major and minor volatiles and sensory analysis of the apricot brandies showed important differences between the samples. The total sensory scores of the apricot brandies ranged between 16.88 for the control sample to 18.35 for the sample produced with the SB yeast strain and diammonium phosphate as nutrient. All the samples of apricot brandies fulfilled EU requirements as regards their content of methanol and other components, such as acetaldehyde, ethyl acetate, and higher alcohols.

The leaf cuticular waxes of 3 poplar clones (Populus euramericana-Pannonia (M1), and Populus deltoides PE 19/66 and B229 (Bora)) were characterized by gas chromatography-mass spectrometry method. Poplar clones grown under identical environmental conditions showed almost identical chemical content of organic compounds within analyzed leaf cuticular wax. The dominant compound was nonacosane, with range from 72,61% ± 0,02 quantified in Pannonia clone to 78,40% ± 0,35 in B229 clone, in total cuticular wax content. Other identified compounds were hexacosane, untriacontane, octacosane, tetradecanal and triacontane; the last, triacontane, was present in very small percentage in wax content, around 1% in all three clones., Površinski voskovi sa lišća od 3 klona topola (Populus euramericana cl. Pannonia (M1) i Populus deltoides cl. PE 19/66 i cl. B229 (Bora)) su analizirani metodom gasnomasene hromatografije. Klonovi topola su uzgajani pod istim uslovima spoljašnje sredine i pokazali gotovo identičan hemijski sastav u okviru analiziranog površinskog voska sa lišća. Dominantno jedinjenje je nonakozan, sa opsegom od 72,61 % ± 0,02 u klonu Pannonia do 78,40 % ± 0,35 u B229 klonu, u odnosu na ukupni hemijski sastav površinskog voska. Druga identifikovana jedinjenja su heksadekan, hentriakontan, oktadekan, tetradekanal i triakontan i poslednji, triakontan je bio prisutan u veoma malom procentu u ukupnom sadržaju površinskog voska, oko 1 % u sva tri klona.