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A sonication method is compared with a microwave-assisted extraction method for recovering polycyclic aromatic hydrocarbons and aliphatic hydrocarbons from seaweed and acid humic samples. Different extracting solvents and adsorbents for the purification step are tested. For the sonication extraction, 10 g of the sample are extracted in an ultrasonic bath (60 degrees C for 15 min with 20 mL of hexane). For the microwave-assisted extraction two steps are carried out, each step at 90 degrees C under pressure in closed vessels with 20 mL of hexane for 10 min at 950 W. A clean-up step is performed for both extraction techniques. The results indicate that the recovery of hydrocarbons is dependent on both the extraction technique and the type of matrix. The most suitable technique appears to be sonication employing hexane as the extraction solvent. The recoveries obtained for aliphatic hydrocarbons are higher than those achieved for the polycyclic aromatic hydrocarbons, with values ranging within 81-109% and 40-76%, respectively.

Pheromones play a crucial role in mate stimulation and discrimination. In the fruit fly Drosophila, the most abundant cuticular hydrocarbons act as sex pheromones during courtship behavior. There are several active molecules and they compose a sex- and species-specific pheromonal bouquet. Different species from the Drosophila melanogaster subgroup have adopted alternative systems of chemical mate recognition. Recent exploration of these interspecific variations, and of intraspecific variations, has led to the characterization of genes and to the mapping of structures that process the production and perception of chemical messages.

Gas chromatography has been used to analyze the variation in cuticular hydrocarbon patterns between several populations of Amblyomma cajennense. 88 compounds were detected and these could be divided into 17 groups of hydrocarbons. Heterozygosis in the populations ranges from 0% to 25.84%. Isomers for pentacosane, heptacosane and nonatriacontane are the most variable, with 13, 10 and 11 variants, respectively. Nei's genetic identity and genetic distance show that populations may be considered as regional variants of only one species: the results do not indicate the presence of sibling species. However, a relatively high genetic distance has been observed between several Cuban and continental populations, suggesting a long reproductive isolation. Gas chromatography of cuticular hydrocarbons is a good alternative to isozyme analysis for population studies, when collecting conditions do not allow the use of live ticks and only alcohol-preserved collections are available. The high number of compounds available for genetic studies will provide excellent markers for evaluating the extent of gene flow and migration of tick species.

Lukins, H. B. (University of Texas, Austin) and J. W. Foster. Methyl ketone metabolism in hydrocarbon-utilizing mycobacteria. J. Bacteriol. 85: 1074-1087. 1963.-Species of Mycobacterium especially M. smegmatis 422, produced the homologous methyl ketones during the oxidation of propane, n-butane, n-pentane, or n-hexane. A carrier-trapping experiment demonstrated the formation of 2-undecanone, as well as 1,11-undecanedioic acid, during the oxidation of undecane-1-C(14). Aliphatic alkane-utilizing mycobacteria were able to grow at the expense of several aliphatic methyl ketones as sole sources of carbon. Other ketones which did not support growth were oxidized by resting bacterial suspensions. M. smegmatis 422 cells grown on propane or acetone were simultaneously adapted to oxidize both substrates, as well as n-propanol. n-Propanol cells were unadapted to propane or acetone. Acetone produced from propane in a medium enriched in D(2)O contained a negligible quantity of D, presumably eliminating propylene as an intermediate in the oxidation. Cells grown at the expense of alkanes or methyl ketones in the presence of O(2) (18) had a higher content of O(18) than did cells grown on terminally oxidized compounds, e.g., primary alcohols or fatty acids. An oxygenase reaction is postulated for the attack on methyl ketones. Acetol was isolated and characterized as an oxidation product of acetone by M. smegmatis 422. Acetol-grown cells had a higher O(18) content than did n-propanol cells, and its utilization appears to involve at least one oxygenase reaction. Acetol produced from acetone in the presence of O(2) (18) was not enriched in the isotope, indicating the occurrence of exchange reactions or of oxygenation reactions at a later stage in the assimilation of acetone and acetol.

No variation in total amounts of those polycyclic hydrocarbons with ultraviolet absorption maxima at 385 mmicro was found in the smoke from cigarettes containing varying amounts of hexane solubles. Addition of C(l4)-labeled tobacco paraffins to cigarettes showed that tobacco paraffins are unimportant as precursors of polycyclic hydrocarbons in smoke.

1. The biologic experiments with the links of the methane series-n-pentane, n-hexane, n-heptane, n-octane, i-octane, and pentene-gave these qualitative results: (a) The higher the number of CH(2) groups, the longer the chain, the longer the average lifetime of the animal. (b) The ramified chain does not appear to act differently from the saturated straight chain with the same number of C atoms. (c) One double bond within the chain shortens the lifetime to a considerable degree. 2. The quantitative discussion shows that the lifetimes depend exponentially on the molecular weight. 3. Qualitatively the hypothesis is supported that with rising molecular weight the concentration of CH(2) groups within the animal diminishes according to the vapor pressure or the thermodynamic potential. However, lifetime and these physical properties obey different functions. 4. These physical properties are of high biologic importance. But they are not sufficient to explain the biologic effects quantitatively.

Metal–organic frameworks (MOFs) have been proposed as a promising material for non‐thermal chemical separations owing to their high structural diversity and tunability. Here, we report the synthesis of a zinc‐based MOF containing a three‐dimensional (3D) linker, bicyclo[2.2.2]octane‐1,4‐dicarboxylic acid, with high thermal stability towards the separation of hexane isomers. The incorporation of the 3D linker enhances the structural stability and provides well‐defined pore apertures/channels with sub‐Ångstrom precision. This precision allowed for the separation of similarly sized hexane isomers based on subtle differences in their kinetic diameters. Multi‐component liquid phase batch experiments confirmed the separation of hexanes mixture into linear, monobranched, and dibranched isomers. This work represents a significant milestone in the construction of stable Zn‐based MOFs and the incorporation of 3D linkers as a potential solution to challenging separations. [ABSTRACT FROM AUTHOR]

Cotton gin trash (CGT), a waste product of cotton gins, make up about 10% of each bale of cotton bolls ginned. The current study investigates high value volatile compounds in CGT to add value to this by-product. The volatile compounds in CGT and different parts of the cotton plant were extracted using various methods, identified by gas chromatography-mass spectrometry (GC-MS) or nuclear magnetic resonance (NMR) spectroscopy, and then quantified by gas chromatography-flame ionisation detection (GC-FID) against available standards. Terpenoids including monoterpenoids and sesquiterpenoids were found to be the most abundant, making up 64.66% (area under peak) of total volatiles extracted by hydro-distillation. The major extractable terpenoids in CGT were α-pinene (13.69–23.05 μg/g), β-caryophyllene (3.99–74.32 μg/g), α-humulene (2.00–25.71 μg/g), caryophyllene oxide (41.50–102.08 μg/g) and β-bisabolol (40.05–137.32 μg/g). Recoveries varied between different extraction methods. The terpenoids were found to be more abundant in the calyx (659.12 μg/g) and leaves (627.72 μg/g) than in stalks (112.97 μg/g) and stems (24.24 μg/g) of the cotton plant, indicating the possible biological origin of CGT volatiles. This study is the first to identify and quantify the different terpenoids present in CGT and significantly, β-bisabolol, an abundant compound (sesquiterpene alcohol) which may have valuable biological prospects. These findings therefore contribute to identifying alternative management strategies and uses of CGT. [ABSTRACT FROM AUTHOR]

Royal recognition is a central feature of insect societies, allowing them to maintain the reproductive division of labor and regulate colony demography. Queen recognition has been broadly demonstrated and queen recognition pheromones have been identified in social hymenopterans, and in one termite species. Here we describe behaviors that are elicited in workers and soldiers by neotenic queens and kings of the subterranean termite, Reticulitermes flavipes, and demonstrate the chemical basis for the behavior. Workers and soldiers readily perform a lateral or longitudinal shaking behavior upon antennal contact with queens and kings. When royal cuticular chemicals are transferred to live workers or inert glass dummies, they elicit antennation and shaking in a dose-dependent manner. The striking response to reproductives and their cuticular extracts suggests that royal-specific cuticular compounds act as recognition pheromones and that shaking behavior is a clear and measurable queen and king recognition response in this termite species. [ABSTRACT FROM AUTHOR]

The colder regions of Earth are inhabited by cold-adapted microorganisms designated as psychrophiles that are known to produce cold-active enzymes, such as peptidases, chaperones, lipases, cellulases, and phosphatases. These types of enzymes are a major part of the market of industrial enzymes. Bacteria isolated from water samples collected from the Chamba region in the Himalayas were screened for peptidase production using skim milk agar plates. Among the peptidase-producing bacteria isolated, 20% of the isolates exhibited fast growth and maximum zones of clearance, and thus, were used for further studies. The 16S rDNA sequence analysis of isolate S1DI 10 identified it as a Bacillus sp. The peptidase was cloned in pET28a vector and expressed in Escherichia coli BL21(DE3) and the His-tagged recombinant protein was purified using Ni-NTA column. The purified peptidase of SIDI 10 was found to be an alkaline, cold-active peptidase with optimal enzyme activity at 10°C and pH 8. An approach of one variable at a time was used to further study the effect of various metal ions, organic solvents and detergents on the peptidase enzyme. The peptidase activity was enhanced in the presence of Fe2+ and Mn2+ (metal ions), hexane (organic solvent), SDS- sodium dodecyl sulfate (anionic detergent) and Tween 80 (nonionic detergent). Response surface methodology (RSM) was used to determine the cumulative effect of these five variables. A 25 full factorial central composite design was applied for the five independent variables to determine the optimal combinations of these constituents at the maximum peptidase activity. [ABSTRACT FROM AUTHOR]

Substrate tolerance of bacterial cyclases has been demonstrated in various contexts, but little is known about that of plant cyclases. Here, we tested two plant ε-cyclases to convert C50-lycopene, which we previously established by rounds of directed evolution. Unlike bacterial β-cyclases, two-end cyclase from lettuce exhibited complete specificity against this molecule, indicating that this enzyme has some mechanism that exerts size-specificity. Arabidopsis one-end cyclase At-y2 showed detectable activity to C50-lycopene. Interestingly, we found that it functions as a two-end cyclase in a C50 context. Based on this observation, a possible model for substrate discrimination of this enzyme is proposed. [ABSTRACT FROM AUTHOR]

Oviparous animals across many taxa have evolved diverse strategies that deter egg predation, providing valuable tests of how natural selection mitigates direct fitness loss. Communal egg laying in nonsocial species minimizes egg predation. However, in cannibalistic species, this very behavior facilitates egg predation by conspecifics (cannibalism). Similarly, toxins and aposematic signaling that deter egg predators are often inefficient against resistant conspecifics. Egg cannibalism can be adaptive, wherein cannibals may benefit through reduced competition and added nutrition, but since it reduces Darwinian fitness, the evolution of anticannibalistic strategies is rife. However, such strategies are likely to be nontoxic because deploying toxins against related individuals would reduce inclusive fitness. Here, we report how D. melanogaster use specific hydrocarbons to chemically mask their eggs from cannibal larvae. Using an integrative approach combining behavioral, sensory, and mass spectrometry methods, we demonstrate that maternally provisioned pheromone 7,11-heptacosadiene (7,11-HD) in the eggshell’s wax layer deters egg cannibalism. Furthermore, we show that 7,11-HD is nontoxic, can mask underlying substrates (for example, yeast) when coated upon them, and its detection requires pickpocket 23 (ppk23) gene function. Finally, using light and electron microscopy, we demonstrate how maternal pheromones leak-proof the egg, consequently concealing it from conspecific larvae. Our data suggest that semiochemicals possibly subserve in deceptive functions across taxa, especially when predators rely on chemical cues to forage, and stimulate further research on deceptive strategies mediated through nonvisual sensory modules. This study thus highlights how integrative approaches can illuminate our understanding on the adaptive significance of deceptive defenses and the mechanisms through which they operate. [ABSTRACT FROM AUTHOR]

Bagrada hilaris Burmeister, is a stink bug native to Asia and Africa and invasive in the United States, Mexico, and more recently, South America. This species can cause serious damage to various vegetable crops in the genus Brassica, with seedlings being particularly susceptible to B. hilaris feeding activity. In this study, the role of volatile organic compounds (VOCs) emitted by seedlings of three Brassica species on the host preference of B. hilaris was evaluated. In dual choice arena and olfactometer bioassays, adult painted bugs preferred B. oleracea var. botrytis and B. napus over B. carinata. Volatiles from B. oleracea seedlings were collected and bioassayed with B. hilaris adults and late stage nymphs, using electroantennographic (EAG) and behavioral (olfactometer) techniques. When crude extracts of the VOCs from B. oleracea var. botrytis seedlings and liquid chromatography fractions thereof were bioassayed, B. hilaris adults and nymphs were attracted to the crude extract, and to a non-polar fraction containing hydrocarbons, whereas there were no responses to the more polar fractions. GC-MS analysis indicated that the main constituent of the non-polar fraction was an as yet unidentified diterpene hydrocarbon, with trace amounts of several other diterpene hydrocarbons. The major diterpene occurred in VOCs from both of the preferred host plants B. oleracea and B. napus, but not in VOCs of B. carinata. Our results suggest that this diterpene, alone or in combination with one or more of the minor compounds, is a key mediator in this insect-plant interaction, and could be a good candidate for use in lures for monitoring B. hilaris in the field. [ABSTRACT FROM AUTHOR]

Sulfamethazine (SMZ) (1) is an antibacterial sulfa drug which suppresses the synthesis of dihydrofolic acid. It is used for the treatment of infections in livestock; such as gastrointestinal, and respiratory tract infections. During the current study, synthesis, characterization, and evaluation of immunomodulatory activities of derivatives of sulfamethazine (SMZ) (3–39) was carried out. These derivatives were synthesized by the reaction of sulfamethazine with a range of acid chlorides. All the compounds were characterized by using modern spectroscopic techniques, such as 1H-, and 13C-NMR, EI-MS, and HRFAB-MS. Compounds 3–10, 14, and 15 were identified as new compounds. Immunomodulatory effect of compounds 3–39 on different parameters of innate immune response was evaluated, including the production of Reactive Oxygen Species (ROS) from human whole blood and isolated polymorphonuclear neutrophils (PMNs), nitric oxide (NO), and pro-inflammatory cytokine TNF-α. All the new compounds, except 14 and 15, showed a significant anti-inflammatory activity. Compounds 3–39 were also evaluated for their anti-bacterial activity and cytotoxicity (3T3 mouse fibroblast cell lines). All the compounds were found to be non-cytotoxic against normal cell lines. [ABSTRACT FROM AUTHOR]

Matricaria discoidea DC. (Asteraceae) has documented use as an insect repellent by Blackfoot Indians and other indigenous groups of North America. This investigation was conducted to evaluate this practice and systematically identify chemical constituents responsible for any insect repelling effect by utilizing a mosquito (Aedes aegypti (Linnaeus)) biting deterrent bioactivity-directed purification approach. Hydrodistilled oil from dried aerial parts of M. discoidea was the most bioactive crude extract generated and was as. Fractionation of this extract, followed by re-evaluation for mosquito biting deterrence using the K & D (Klun and Debboun) bioassay, produced many active fractions that were subsequently evaluated by spectroscopic techniques and the most active compounds were determined to be α-terpineol, spathulenol, and neryl isovalerate. A & K (Ali and Khan) large cage in vitro evaluation of pure compounds isolated from M. discoidea indicated α-terpineol to be the most active compound providing complete protection at 25 μg/cm2. This is the first report on the mosquito repellency of neryl isovalerate and scientific evidence reported here validates the traditional use of M. discoidea as a biting-insect deterrent. [ABSTRACT FROM AUTHOR]

In this study, we investigated the anti-microbial, anti-inflammatory, and anti-lipogenic effects of hemp (Cannabis sativa L.) seed hexane extracts, focusing on the Propionibacterium acnes-triggered inflammation and lipogenesis. Hemp seed hexane extracts (HSHE) showed anti-microbial activity against P. acnes. The expression of iNOS, COX-2, and the subsequent production of nitric oxide and prostaglandin increased after infection of P. acnes in HaCaT cells, however, upon treating with HSHE, their expressions were reduced. P. acnes-induced expressions of IL-1β and IL-8 were also reduced. HSHE exerted anti-inflammatory effects by regulating NF-κB and MAPKs signaling and blunting the translocation of p-NF-κB to the nucleus in P. acnes-stimulated HaCaT cells. Moreover, P. acnes-induced phosphorylation of ERK and JNK, and their downstream targets c-Fos and c-Jun, was also inhibited by HSHE. In addition, the transactivation of AP-1 induced by P. acnes infection was also downregulated by HSHE. Notably, HSHE regulated inflammation and lipid biosynthesis via regulating AMPK and AKT/FoxO1 signaling in IGF-1-induced inflammation and lipogenesis of sebocytes. In addition, HSHE inhibited 5-lipoxygenase level and P. acnes-induced MMP-9 activity, and promoted collagen biosynthesis in vitro. Thus, HSHE could be utilized to treat acne vulgaris, through its anti-microbial, anti-inflammatory, anti-lipogenic, and collagen-promoting properties. [ABSTRACT FROM AUTHOR]

Background: Hyperurecemia is usually associated with gout and various metabolic arthritis disorders. Limited medications are available to manage such conditions. This study aimed to isolate the triterpenes constituent of the plant and to assess xanthine oxidase (XO) inhibitory and antihyperuricemic activities of Tribulus arabicus ethanolic extract, its fractions and the isolated compound using in vitro and in vivo approaches. Methods: The ethanolic extract, fractions; n-hexane, chloroform and n-butanol and the isolated compound (ursolic acid) were evaluated in vitro for their XO inhibitory activity. Those that demonstrated significant activity were further evaluated for their antihyperuricemic activity on potassium oxonate-induced hyperuricemia in mice. Results: The ethanolic extract was found to be safe up to 5000 mg/kg. The extract and its n-hexane fraction exhibited significant inhibitory activity on XO, whilst only a modest reduction in the enzymatic activity was noticed with n-butanol and chloroform fractions. Furthermore, administration of the ethanolic extract at low and high doses significantly reduced serum urate levels in mice by 31.1 and 64.6% respectively. The isolated active constituent, ursolic acid, showed potent XO inhibition activity (Half maximal inhibitory concentration, IC50 = 10.3 μg/mL), and significantly reduced uric acid level in vivo by 79.9%. Virtually, the binding mode of ursolic acid with XO was determined using molecular docking simulations. Conclusions: The activity of the ethanolic extract of T. arabicus and its n-hexane fraction can be attributed to the isolated compound, ursolic acid. Ursolic acid has good hypouricemic activity and therefore has high potential to be used for the treatment of gout and hyperuricemia-related diseases. [ABSTRACT FROM AUTHOR]

The chemicals emitted from the sex pheromone gland of individual Heliothis subflexa females were sampled using a short section of thick-film megabore fused silica capillary column, and the pheromone glands of the same females were extracted after the effluvia collection. Both samples were treated with a silylation reagent, and then subjected to gas chromatography-chemical ionization-mass spectrometry for quantitative and qualitative analysis of all components. The total amount of all 11 components emitted from the glands of calling females was 153 ng/female/hr, which was substantially higher than previously reported. The ratios of the pheromone components in the volatile emissions and pheromone gland extracts were generally similar to previous studies, but with notable differences. The collections of volatiles and gland extractions contained, respectively: Z9-14:Ald (1.57%, 1.35%), 14:Ald (3.78%, 1.51%), Z7 + Z9-16:Ald (9.60%, 3.59%), Z11-16:Ald (76.14%, 18.94%), 16:Ald (2.95%, 2.17%), Z9-16:OH (0.07%, 7.21%), Z11-16:OH (1.11%, 49.04%), Z7-16:OAc (0.48%, 1.73%), Z9-16:OAc (1.32%, 4.02%), and Z11-16:OAc (2.98%, 10.43%). The thick-film megabore column is an efficient approach for sampling the headspace for semiochemicals. [ABSTRACT FROM AUTHOR]

Mycolic acids (MA) are major, species-specific lipid components of Mycobacteria and related genera. In Mycobacterium tuberculosis, it is made up of alpha-, methoxy- and keto-MA, each with specific biological functions and conformational characteristics. Antibodies in tuberculosis (TB) patient sera respond differently towards the three MA classes and were reported to cross-react with cholesterol. To understand the antigenicity and cholesterol cross-reactivity of MA, we generated three different chicken -derived phage-displayed single-chain variable fragments (scFv) that reacted similarly towards the natural mixture of MA, but the first recognized all three classes of chemically synthetic MAs, the second only the two oxygenated types of MAs and the third only methoxy MA. The cholesterol cross-reactivity was investigated after grafting each of the three scFv types onto two configurations of constant chain domains–CH1-4 and CH2-4. Weak but significant cross-reactivity with cholesterol was found only with CH2-4 versions, notably those two that were also able to recognize the trans-keto MA. The cholesteroid nature of mycobacterial mycolic acids therefore seems to be determined by the trans-keto MA subclass. The significantly weaker binding to cholesterol in comparison to MA confirms the potential TB diagnostic application of these antibodies. [ABSTRACT FROM AUTHOR]

Background: Ivermectin is the only drug currently recommended for the treatment of onchocerciasis, the second leading infectious cause of blindness in the world. This drug kills only the first stage larvae—microfilariae (mf) of Onchocerca volvulus and is to be used cautiously in areas where Loa loa is prevalent because of severe adverse events observed with coinfected patients. Methodology/Principal findings: This study investigated the anti-filarial activities of two Cameroonian medicinal plants, Lantana camara and Tamarindus indica locally used to treat onchocerciasis. Twelve (12) extracts were prepared and tested in vitro on the bovine model parasite, O. ochengi as well as L. loa mf. Both mf and adult male worm viabilities were assessed by motility scoring, while adult female worm viability was determined biochemically by standard MTT/formazan colorimetry. Cytotoxicity and acute toxicity were determined respectively, in monkey kidney epithelial cells and in BALB/c mice. Pure compounds were isolated by LC/MS using a bio-assay guided strategy. All the extracts showed 100% activity at 500 μg/mL against O. ochengi adult worms and mf. The highest activity against O. ochengi was observed with the hexane extract of L. camara leaves (LCLhex), with IC50 of 35.1 μg/mL for adult females and 3.8 μg/mL for the mf. Interestingly, this extract was more active against O. ochengi mf than L. loa mf. Further studies on the extracts led to the isolation of lantadene A from the methylene chloride extract of L. camara leaves, with IC50s of 7.85 μg/mL for adult males, 10.38 μg/mL for adult females, 10.84 μg/mL for O. ochengi mf and 20.13 μg/mL for L. loa mf. Conclusions/Significance: We report for the first time the anti-onchocercal activities of these locally consumed medicinal plants and lantadene A, a potential lead for further development as an onchocerciasis cure. [ABSTRACT FROM AUTHOR]

The aim of this study is to disclose the potential bioactive components of Cuscuta palaestina, a native parasitic natural plant of flora palaestina and to open direction towards new prospective application. GC-MS analysis identified 18 components in the methanolic extract of C. palaestina for the first time. The most appealing among them are Sesamin and two other phytosterols (Campesterol and Stigmasterol), all of which are documented in the scientific literature for their anticancer activity. Quantitation of Sesamin extracted from C. palaestina by HPLC-PDA with the use of three organic solvents showed that the Sesamin content in the methanolic extract was the highest. Following the disclosure of Sesamin presence in C. palaestina, we raised the question of whether it is produced naturally in C. palaestina or acquired from the host plant. The quantitation of Sesamin in C. palaestina was performed while being with five different host plants, and was compared with the amount of Sesamin in C. palaestina grown alone. The findings reveal that Sesamin is an endogenous secondary metabolite in C. palaestina. Thus, further studies are required to prove if C. palaestina can be used as an alternative source of anticancer phytochemicals, mainly Sesamin, and if proteins in the Sesamin production pathway could be valid biological targets for the development of novel and selective pesticides for control/ eradication of C. palaestina and maybe some other Cuscuta species. As well, the findings from this study raise a big question of whether inferring Sesamin production in C. palaestina could reduce its attack ability to host plants. [ABSTRACT FROM AUTHOR]

Insect cuticular hydrocarbons (CHCs) play critical roles in reducing water loss and chemical communication. Species-specific CHC profiles have been used increasingly as an excellent character for species classification. However, considerably less is known about their potential for population delimitation within species. The aims of this study were to develop a solid-phase microextraction (SPME)-based CHC collection method and to investigate whether CHC profiles could serve as potential chemotaxonomic tools for intraspecific delimitation in Acyrthosiphon pisum. Optimization of fibers for SPME sampling revealed that 7 μm polydimethylsiloxane (PDMS) demonstrated the most efficient adsorption of CHCs among five different tested fibers. SPME sampling showed good reproducibility with repeated collections of CHCs from a single aphid. Validation of SPME was performed by comparing CHC profiles with those from conventional hexane extractions. The two methods showed no qualitative differences in CHCs, although SPME appeared to extract relatively fewer short-chained CHCs. While CHC profiles of a given population differed among developmental stages, wing dimorphism types, and host plants, wingless adult aphids showed very low variance in relative proportions of individual CHC components. Reproducibility of CHC profiles was explored further to classify wingless adult morphs of A. pisum from five different geographic regions that showed no variation in mitochondrial COI gene sequences. Our results demonstrate that CHC profiles are useful in intraspecific delimitation in the field of insect chemotaxonomy. [ABSTRACT FROM AUTHOR]

In view of the few reports concerning aromatic nucleophilic substitution reactions featuring an alkoxy group as a leaving group, the aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene was investigated with a bulky t-butoxide nucleophile under microwave irradiation. The transetherification of 2,4-dimethoxynitrobenezene with sodium t-butoxide under specific conditions, namely for 20 min at 110°C in 10% dimethoxyethane in toluene, afforded the desired product in 87% yield with exclusive ortho-selectivity. A variety of reaction conditions were screened to obtain the maximum yield. The aromatic nucleophilic substitution of 2,4-dimethoxynitrobenzene with t-butoxide should be carried out under controlled conditions in order to avoid the formation of byproducts, unlike that of dihalogenated activated benzenes. Among the formed byproducts, a major compound was elucidated as 2,4-dimethoxy-N-(5-methoxy-2-nitrophenyl)aniline by X-ray crystallography. [ABSTRACT FROM AUTHOR]

In the current study two novel psychrophilic diatoms Porosira glacialis and Attheya longicornis were tested for suitability to CO2 mitigation coupled with production of the physiologically requisite omega– 3 fatty acids. This study is in line with the worldwide conducted research aimed at applying biorefinery concept to heavy polluting industries. Since the production of algal high value compounds, i.e. essential fatty acids, relies on utilization of residual CO2 emissions coming from industry, the costs of such production maybe substantially reduced. Besides, the ecological benefits of the biorefinery concept being implemented are obvious, since CO2 is one of the major greenhouse gases. The current research has shown that one of the tested microalgal species, the diatom P. glacialis showed good tolerance to high (20–25%) levels of CO2 and maintained growth rates comparable to controls. The total lipid content in the CO2 aerated culture increased from 8.91 to 10.57% in cell dry mass. Additionally, the content of docosahexaenoic acid (DHA) increased from 3.90 to 5.75%, while the concentration of eicosapentaenoic acid (EPA) decreased from 26.59 to 23.66%. In contrast, A. longicornis did not demonstrate any significant increase in total lipid content. Besides, its growth was hampered by high levels of CO2 aeration. [ABSTRACT FROM AUTHOR]

Castniid moths (Lepidoptera: Castniidae) display a butterfly-like reproductive behavior, i.e., they use visual stimuli for mate location and females have apparently lost their pheromone glands in an evolutionary context. In this paper we report for the first time the identification of three new compounds, namely n-octadecyl acetate, (Z)-9-octadecenyl acetate and (E,Z)-2,13-octadecadienyl acetate, in males of the Castniid Palm Borer, Paysandisia archon, which could be involved in its short-range courtship behavior, and also shed light on recent controversies on the sexual behavior of the species. The compounds are produced in a ring-shaped gland of the male terminalia and have occasionally been detected in very minor amounts (ng) in ovipositor extracts of females, but only while mating or just after copulation. We also report that males use the already known (E,Z)-2,13-octadecadienol to mark their territory by rubbing their midlegs against the upper side of nearby leaves, especially palm leaves. This compound, produced in large amounts, is mostly concentrated in the midleg basitarsi and its maximum production is detected on the sexually mature 1-day-old specimens. In addition, analysis of male wings extracts confirms the presence of Z,E and E,E-farnesals, which are mostly produced in the median band of hindwings of 48–53 h-old insects. The biological significance of farnesals in this species is unknown. Our results point out that the chemical communication of P. archon relies mostly on males, which appear to bear all chemical burden in this respect. [ABSTRACT FROM AUTHOR]

In the past decades, the sex pheromone composition in female moths has been analyzed by different methods, ranging from volatile collections to gland extractions, which all have some disadvantage: volatile collections can generally only be conducted on (small) groups of females to detect the minor pheromone compounds, whereas gland extractions are destructive. Direct-contact SPME overcomes some of these disadvantages, but is expensive, the SPME fiber coating can be damaged due to repeated usage, and samples need to be analyzed relatively quickly after sampling. In this study, we assessed the suitability of cheap and disposable fused silica optical fibers coated with 100 μm polydimethylsiloxane (PDMS) by sampling the pheromone of two noctuid moths, Heliothis virescens and Heliothis subflexa. By rubbing the disposable PDMS fibers over the pheromone glands of females that had called for at least 15 minutes and subsequently extracting the PDMS fibers in hexane, we collected all known pheromone compounds, and we found a strong positive correlation for most pheromone compounds between the disposable PDMS fiber rubs and the corresponding gland extracts of the same females. When comparing this method to volatile collections and the corresponding gland extracts, we generally found comparable percentages between the three techniques, with some differences that likely stem from the chemical properties of the individual pheromone compounds. Hexane extraction of cheap, disposable, PDMS coated fused silica optical fibers allows for sampling large quantities of individual females in a short time, eliminates the need for immediate sample analysis, and enables to use the same sample for multiple chemical analyses. [ABSTRACT FROM AUTHOR]

We report the identification, synthesis, and field bioassay of a novel attractant pheromone produced by males of Eburodacrys vittata (Blanchard), a South American cerambycid beetle in the subfamily Cerambycinae. Headspace volatiles from males contained a sex-specific compound, identified as 10-methyldodecanal. In a field bioassay conducted in Brazil, significant numbers of males and females were caught in traps baited with synthesized racemic 10-methyldodecanal, consistent with the aggregation-sex pheromones produced by males of many cerambycine species. This compound represents a new structural class of cerambycid pheromones, and it is the first pheromone identified for a species in the tribe Eburiini. [ABSTRACT FROM AUTHOR]

Scurrula ferruginea (Jack) Danser is one of the mistletoe species belonging to Loranthaceae family, which grows on the branches of many deciduous trees in tropical countries. This study evaluated the antioxidant activities of S. ferruginea extracts. The cytotoxic activity of the selected extracts, which showed potent antioxidant activities, and high phenolic and flavonoid contents, were investigated in human breast cancer cell line (MDA-MB-231) and non-cancer human skin fibroblast cells (HSF-1184). The activities and characteristics varied depending on the different parts of S. ferruginea, solvent polarity, and concentrations of extracts. The stem methanol extract showed the highest amount of both phenolic (273.51 ± 4.84 mg gallic acid/g extract) and flavonoid contents (163.41 ± 4.62 mg catechin/g extract) and strong DPPH• radical scavenging (IC50 = 27.81 μg/mL) and metal chelation activity (IC50 = 80.20 μg/mL). The stem aqueous extract showed the highest ABTS•+ scavenging ability. The stem methanol and aqueous extracts exhibited dose-dependent cytotoxic activity against MDA-MB-231 cells with IC50 of 19.27 and 50.35 μg/mL, respectively. Furthermore, the extracts inhibited the migration and colony formation of MDA-MB-231 cells in a concentration-dependent manner. Morphological observations revealed hallmark properties of apoptosis in treated cells. The methanol extract induced an increase in ROS generation and mitochondrial depolarization in MDA-MB-231 cells, suggesting its potent apoptotic activity. The present study demonstrated that the S. ferruginea methanol extract mediated MDA-MB-231 cell growth inhibition via induction of apoptosis which was confirmed by Western blot analysis. It may be a potential anticancer agent; however, its in vivo anticancer activity needs to be investigated. [ABSTRACT FROM AUTHOR]

The 2-aminothiazole series has anti-bacterial activity against the important global pathogen Mycobacterium tuberculosis. We explored the nature of the activity by designing and synthesizing a large number of analogs and testing these for activity against M. tuberculosis, as well as eukaryotic cells. We determined that the C-2 position of the thiazole can accommodate a range of lipophilic substitutions, while both the C-4 position and the thiazole core are sensitive to change. The series has good activity against M. tuberculosis growth with sub-micromolar minimum inhibitory concentrations being achieved. A representative analog was selective for mycobacterial species over other bacteria and was rapidly bactericidal against replicating M. tuberculosis. The mode of action does not appear to involve iron chelation. We conclude that this series has potential for further development as novel anti-tubercular agents. [ABSTRACT FROM AUTHOR]

Aedes aegypti, Aedes albopictus and Culex quinquefasciatus are vectors of dengue fever and West Nile virus diseases. This study was conducted to determine the toxicity, mechanism of action and the binding interaction of three active phenylpropanoids from Piper sarmentosum (Piperaceae) toward late 3rd or early 4th larvae of above vectors. A bioassay guided-fractionation on the hexane extract from the roots of Piper sarmentosum led to the isolation and identification of three active phenylpropanoids; asaricin 1, isoasarone 2 and trans-asarone 3. The current study involved evaluation of the toxicity and acetylcholinesterase (AChE) inhibition of these compounds against Aedes aegypti, Aedes albopictus and Culex quinquefasciatus larvae. Asaricin 1 and isoasarone 2 were highly potent against Aedes aegypti, Aedes albopictus and Culex quinquefasciatus larvae causing up to 100% mortality at ≤ 15 μg/mL concentration. The ovicidal activity of asaricin 1, isoasarone 2 and trans-asarone 3 were evaluated through egg hatching. Asaricin 1 and isoasarone 2 showed potent ovicidal activity. Ovicidal activity for both compounds was up to 95% at 25μg/mL. Asaricin 1 and isoasarone 2 showed strong inhibition on acetylcholinesterase with relative IC50 values of 0.73 to 1.87 μg/mL respectively. These findings coupled with the high AChE inhibition may suggest that asaricin 1 and isoasarone 2 are neuron toxic compounds toward Aedes aegypti, Aedes albopictus and Culex quinquefasciatus. Further computational docking with Autodock Vina elaborates the possible interaction of asaricin 1 and isoasarone 2 with three possible binding sites of AChE which includes catalytic triads (CAS: S238, E367, H480), the peripheral sites (PAS: E72, W271) and anionic binding site (W83). The binding affinity of asaricin 1 and isoasarone 2 were relatively strong with asaricin 1 showed a higher binding affinity in the anionic pocket. [ABSTRACT FROM AUTHOR]

The sub-dermal secretory cavities (glands) embedded within the leaves of Eucalyptus (Myrtaceae) were once thought to be the exclusive repositories of monoterpene and sesquiterpene oils. Recent research has debunked this theory and shown that abundant non-volatile compounds also occur within foliar glands. In particular, glands of four species in subgenus Eucalyptus contain the biologically active flavanone pinocembrin. Pinocembrin shows great promise as a pharmaceutical and is predominantly plant-sourced, so Eucalyptus could be a potential commercial source of such compounds. To explore this we quantified and assessed the purity of pinocembrin in glands of 11 species of E. subg. Eucalyptus using Electro-Spray Ionisation Liquid Chromatography Mass Spectrometry of acetonitrile extracts and Gas Chromatography Mass Spectrometry analyses of hexane extracts of isolated glands which were free from other leaf tissues. Our results showed that the glands of subgenus Eucalyptus contain numerous flavanones that are structurally related to pinocembrin and often present in much greater abundance. The maximum concentration of pinocembrin was 2 mg g-1 dry leaf found in E. stellulata, whereas that of dimethylpinocembrin (5,7-dimethoxyflavanone) was 10 mg g-1 in E. oreades and that of pinostrobin (5-hydroxy-7-methoxyflavanone) was 12 mg g-1 in E. nitida. We also found that the flavanones are exclusively located within the foliar glands rather than distributed throughout leaf tissues. The flavanones differ from the non-methylated pinocembrin in the degree and positions of methylation. This finding is particularly important given the attractiveness of methylated flavonoids as pharmaceuticals and therapeutics. Another important finding was that glands of some members of the subgenus also contain flavanone O-glucosides and flavanone-β-triketone conjugates. In addition, glands contain free β-triketones, β-triketone heterodimers and chromone C-glucosides. Therefore, the foliar glands of this taxonomically distinct group of plants are a rich source of a range of flavonoids and other biologically active compounds with great commercial potential. [ABSTRACT FROM AUTHOR]

The bark of Mimosa tenuiflora (Willd.) Poiret (Leguminosae family), popularly known as “jurema preta” in Brazil, is used by the population of Contendas of Sincorá (Bahia State, Brazil) for the treatment of coughs and wound healing. Thus, the aim of this study was to evaluate the antinociceptive and anti-inflammatory activities of the bark ethanol extract (EEMT) and solvent soluble fractions (hexane—H, DCM—D, EtOAc—E and BuOH—B) of the extract in vivo. Additionally, we synthesized 5,7-dihidroxy-4’-methoxyflavanone (isosakuranetin) and isolated the compound sakuranetin, and both compounds were also tested. The anti-inflammatory and antinociceptive assays performed were: writhing test; nociception induced by intraplantar formalin injection; leukocyte recruitment to the peritoneal cavity; evaluation of vascular permeability (Evans blue test); and evaluation of mechanical hypernociception (von Frey test). Production of TNF-α, IL-10, myeloperoxidase and the expression of ICAM-1 were also evaluated. Statistical analysis was performed by one-way ANOVA followed by the Bonferroni post-test (n = 8), with P < 0.05. The EEMT showed antinociceptive activities in writhing test (100–200 mg/kg), in the second phase of the formalin test (50–200 mg/kg), and in mechanical hypernociception (100 mg/kg). EEMT showed an anti-inflammatory effect by reducing neutrophil migration to the peritoneal cavity and in the plantar tissue detected by the reduction of myeloperoxidase activity (100 mg/kg), reduction of IL-10 levels and expression of ICAM-1 in the peritoneal exudate and the mesentery (100 mg/kg), respectively. The four soluble EEMT fractions showed good results in tests for antinociceptive (H, D, E, B) and anti-inflammation (H, D, E). Only sakuranetin showed reduction of the writhing and neutrophil migration (200 mg/kg). Thus, the EEMT and soluble fractions of M. tenuiflora bark demonstrated great antinociceptive and anti-inflammatory activities, as also sakuranetin. More studies should be conducted to elucidate the mechanism of action of this compound. To the best of our knowledge, this is the first report on the antinociceptive activity of the M. tenuiflora fractions and the bioactive isolated compound sakuranetin in vivo. [ABSTRACT FROM AUTHOR]

The aim of this study was to design, synthesize and validate a multifunctional antidepressant probe that is modified at two distinct positions. The purpose of these modifications was to allow covalent linkage of the probe to interaction partners, and decoration of probe-target complexes with fluorescent reporter molecules. The strategy for the design of such a probe (i.e., azidobupramine) was guided by the need for the introduction of additional functional groups, conveying the required properties while keeping the additional moieties as small as possible. This should minimize the risk of changing antidepressant-like properties of the new probe azidobupramine. To control for this, we evaluated the binding parameters of azidobupramine to known target sites such as the transporters for serotonin (SERT), norepinephrine (NET), and dopamine (DAT). The binding affinities of azidobupramine to SERT, NET, and DAT were in the range of structurally related and clinically active antidepressants. Furthermore, we successfully visualized azidobupramine-SERT complexes not only in SERT-enriched protein material but also in living cells stably overexpressing SERT. To our knowledge, azidobupramine is the first structural analogue of a tricyclic antidepressant that can be covalently linked to target structures and further attached to reporter molecules while preserving antidepressant-like properties and avoiding radioactive isotopes. [ABSTRACT FROM AUTHOR]