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Every petroleum-processing plant produces sewage sludge containing several types of polycyclic aromatic hydrocarbons (PAHs). The degradation of PAHs via physical, biological, and chemical methods is not yet efficient. Among biological methods, the use of marine sponge symbiont bacteria is considered an alternative and promising approach in the degradation of and reduction in PAHs. This study aimed to explore the potential performance of a consortium of sponge symbiont bacteria in degrading anthracene and pyrene. Three bacterial species ( Bacillus pumilus strain GLB197, Pseudomonas stutzeri strain SLG510A3-8, and Acinetobacter calcoaceticus strain SLCDA 976) were mixed to form the consortium. The interaction between the bacterial consortium suspension and PAH components was measured at 5 day intervals for 25 days. The biodegradation performance of bacteria on PAH samples was determined on the basis of five biodegradation parameters. The analysis results showed a decrease in the concentration of anthracene (21.89%) and pyrene (7.71%), equivalent to a ratio of 3:1, followed by a decrease in the abundance of anthracene (60.30%) and pyrene (27.52%), equivalent to a ratio of 2:1. The level of pyrene degradation was lower than that of the anthracene due to fact that pyrene is more toxic and has a more stable molecular structure, which hinders its metabolism by bacterial cells. The products from the biodegradation of the two PAHs are alcohols, aldehydes, carboxylic acids, and a small proportion of aromatic hydrocarbon components.

Metal-organic frameworks (MOFs) have received extensive attention in adsorption applications owing to their high surface area. However, some MOFs do not perform well as the extraction medium when used under aqueous conditions. The low hydrostability of MOFs limits the practical application of these materials in solid-phase microextraction (SPME). Here, the fabrication of a water resistance SPME fiber coating is introduced based on the crystal violet (CV)-modified HKUST-1 framework on copper (Cu@HKUST-1@CV). The HKUST-1 was prepared by the in situ growth method, followed by post-synthetic modification of HKUST-1 with the CV layer. The preparation of the modified HKUST-1 was characterized by FESEM, XRD, FTIR, and DFT approaches. The prepared SPME coating was successfully employed for the quantification of anthracene (AN), as a model analyte, in water samples. The limit of detection was 0.8 ng mL -1 . The developed method will open up a new door towards searching for promising materials in SPME applications., (© 2021. The Author(s), under exclusive licence to Springer-Verlag GmbH Austria, part of Springer Nature.)

We report on the chemical analysis of a mud dauber wasp nest-associated fungus, Penicillium sp. CMB-MD22, leading to the discovery and structure elucidation of three known ( 1 - 3 ) and two new ( 4 and 5 ) anthrones, and a family of new and known bianthrones, neobulgarones 6 - 23 . Detection and structure elucidation of 1 - 23 was supported by detailed spectroscopic analysis, as well as chemical (thermal) transformations, and global natural products social (GNPS) molecular networking. An empirical approach using HPLC retention times was effective at differentiating anti from syn bianthrone isomers, while a facile thermal equilibration was shown to favor anti over syn isomers. The neobulgarones 6 - 23 are natural products, and a crude extract rich in 6 - 23 exhibits selective antifungal activity against a co-isolated mud dauber wasp nest-associated fungus, suggestive of a possible ecological role as an antifungal chemical defense.

While depsidones, depsides or dibenzofuran-like compounds dominate the chemical composition of lichens, the cyanolichen Nephroma laevigatum affords a diversity of quinoid pigments represented by chlorinated anthraquinones derived from emodin and new bianthrones resulting from the homo- or heterodimerization of monomers. Bianthrones were pointed out from the dichloromethane extract by MS/MS-based molecular networking, then isolated and characterized on the basis of extensive spectroscopic analyzes and GIAO NMR shift calculation followed by CP3 analyzes., (Copyright © 2020 Elsevier B.V. All rights reserved.)

Roasting is an important process in cocoa production which may lead to formation of non-desirable compounds such as polycyclic aromatic hydrocarbons (PAHs). Therefore, PAH4 (sum of four different polycyclic aromatic hydrocarbons; benz[a]anthracene, chrysene, benzo[b]fluoranthene, and benzo[a]pyrene) in roasted cocoa beans was determined using a modified method (combination of QuEChERS and DLLME), and quantified by HPLC-FLD. The modified method was validated and met the performance criteria required by the EU Regulation (No. 836/2011). Results show a significant (p < 0.05) increase of PAH4 (0.19-7.73 ng/g) with an increase in temperatures (110-190 °C) and duration (10-50 min). The PAHs content in whole cocoa bean roasting was detected even at the lowest temperature (110 °C) compared to nib roasting detected at 150 °C which indicates that PAHs was transferred from dried shells to roasted cocoa beans during the roasting process. The data obtained may help to control and minimize PAH4 formation during cocoa processing., (Copyright © 2019 Elsevier Ltd. All rights reserved.)

Separation of naphtodianthrones (NTs) from Hypericum perforatum L. (aerial part of St. John's Wort) is still topical due to some hard-to-beat medicinal attributes of these bioactive compounds. Unfortunately, their low bioavailability (0.06%-0.4%) complicates the extraction process. Therefore, developing straightforward and lower-cost methodologies for NT separation is still a priority. In support of this purpose, for preparing NT formulations from flowers and leaves of wild St. John's Wort (hyperici herba), a cutoff preparative methodology is described herein. Combining Soxhlet extraction and reflux extraction, some concentrated and rather pure NT ethanolic-based formulations without chlorophyl and grease were obtained.

The use of natural products and their derivatives has evolved as a promising approach for the treatment of various infectious diseases, particularly to combat drug-resistant microbial strains. In addition, these natural products characterized by the presence of novel structures and mechanisms of action may provide guidance toward the development of potential new chemotherapies. In the present review, antimicrobial resistance (AMR) is briefly introduced and research focused on the identification and characterization of actinomycete metabolites for antimicrobial activity is discussed. Three compounds, i.e., walkmycin B, waldiomycin, and signamycin B, with novel mechanisms of action as histidine kinase inhibitors, were isolated from the metabolites of actinomycetes. New antituberculosis antibiotics, tuberlactomicin A and caprazamycins, were discovered, and amycolamicin was identified as an antimethicillin-resistant Staphylococus aureus antibiotic. The discovery of these compounds encourages the discovery and investigation of more natural products active against antimicrobial-resistant species, thus providing scaffold for the development of effective drugs against various AMR species.

Five new metabolites, including the xanthone derivative wentixanthone A (1), the benzophenone wentiphenone A (2), the diastereomeric mixtures of the bianthrones wentibianthrone A (3a, b) and wentibianthrone B (4a, b), as well as (10R,10'S)-wentibianthrone C (5a) and (10R,10'R)-wentibianthrone C (5b) were obtained from the fungus Aspergillus wentii, isolated from soil of the hypersaline lake El Hamra in Wadi El-Natrun, Egypt. The structures of the isolated compounds were established by one and two-dimensional NMR and MS spectroscopic analysis. The relative configuration of bianthrones (3-5) was elucidated by comparison of experimental and computed 1 H NMR chemical shifts. Results of biological assays are reported., (Copyright © 2019. Published by Elsevier Ltd.)

An environmentally benign and cost-effective method was designed for isolating and purifying condensed arenes from acetone-extractable portion (AEP) of a high-temperature coal tar through a high pressure preparative chromatograph (HPPC) with different packings, including silica gel, octadecyl silane, octyl bonded silica gel, and diol bonded silica gel. In total, 196 compounds were detected with a gas chromatograph/mass spectrometer from AEP and its eluates. From the eluates, naphthalene, anthracene, phenanthrene, fluoranthene, and pyrene were successfully isolated and purified, and their structures were confirmed by their 1 H and 13 C nuclear magnetic resonance spectra in addition to their mass spectra. Extraction-HPPC device and solvent recovery process were designed and developed, which can potentially be applied to industrial production because the process is easy-to-operate and ecofriendliness. In addition, the solvents used can be easily recovered and reused, and neither waste water nor other pollutions are emitted., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Hydrogen bonding is a vital feature of a large ensemble of chemical structures. Soluble epoxide hydrolase (sEH) has been targeted for development of the treatment for inflammation-associated diseases. Compounds 1 and 2 were purified from Rubia philippinensis, and their structures were established via physical data analysis. Compound 1 possesses intramolecular hydrogen bonding, sufficiently robust to transfer heteronuclear magnetization via a nonbonded interaction. The bonding strength was assessed using the 1 H NMR chemical shift temperature coefficients (-1.8 ppb/K), and the heteronuclear coupling constants were measured. The stereochemical details were investigated using interproton distance analysis and ECD. Purified compounds displayed moderate sEH-inhibitory activity.

Karwinskia parvifolia possesses the highest concentration levels of the anthracenone T-514 (PA1). Studies have demonstrated the induction of apoptosis by PA1 in cancer cell lines. The aim was to investigate the effects of PA1 on the apoptosis of the mouse liver in vivo and its underlying pathway. Sixty CD-1 mice were divided into three groups: untreated, vehicle, and treated with PA1. The animals were euthanized at 4, 8, 12, and 24 h post-treatment. To confirm the toxic effect of PA1 we determined the activity of catalase. Liver sections were prepared for morphological examination and for immunohistochemical evaluation of anti and pro-apoptotic markers. DNA fragmentation was detected by TUNEL assay and electrophoresis. Pre-apoptotic mitochondrial alterations and cytochrome c oxidase activity were analyzed by transmission electron microscopy. PA1 induced pre-apoptotic mitochondrial alterations, a high activity of the cytochrome oxidase, and apoptosis in hepatocytes. PA1 caused p53 over-expression and down regulation of PCNA. PA1 also increased the expression levels of the pro-apoptotic markers Bax and Bak, whereas the anti-apoptotic molecule Bcl-2 was decreased. PA1 induces apoptosis by activating the intrinsic mitochondrial apoptotic pathway. These results will be useful for studies regarding the use of PA1 as an antineoplastic agent., (Copyright © 2018 Elsevier Ltd. All rights reserved.)

Four known compounds, rishirilide B (1), rishirilide C (2), lupinacidin A (3), and galvaquinone B (4), representing two anthracene scaffolds typical of aromatic polyketides, were isolated from a culture of the deep-sea-derived Streptomyces olivaceus SCSIO T05. From the S. olivaceus producer was cloned and sequenced the rsd biosynthetic gene cluster (BGC) that drives rishirilide biosynthesis. The structural gene rsdK 2 inactivation and heterologous expression of the rsd BGC confirmed the single rsd BGC encodes construction of 1-4 and, thus, accounts for two anthracene scaffolds. Precursor incubation experiments with 13 C-labeled acetate revealed that a Baeyer-Villiger-type rearrangement plays a central role in construction of 1-4. Two luciferase monooxygenase components, along with a reductase component, are presumably involved in the Baeyer-Villiger-type rearrangement reaction enabling access to the two anthracene scaffold variants. Engineering of the rsd BGC unveiled three SARP family transcriptional regulators, enhancing anthracene production. Inactivation of rsdR 4 , a MarR family transcriptional regulator, failed to impact production of 1-4, although production of 3 was slightly improved; most importantly rsdR 4 inactivation led to the new adduct 6 in high titer. Notably, inactivation of rsdH, a putative amidohydrolase, substantially improved the overall titers of 1-4 by more than 4-fold.

In the quest for bioactive natural products of fungal origin, Aspergillus flavus was isolated from rhizosphere of Mentha piperita using Potato Dextrose Agar (PDA) and Czapec Yeast Broth (CYB) nutrient media for metabolites production. In total, three different metabolites were purified using HPLC/LCMS and the structures were established using 500 Varian NMR experiments. Further the isolated metabolites in different concentrations (10, 100, 1000 μg/mL) were tested for herbicidal activity using Completely Randomized design (CRD) against the seeds of Silybum marianum and Avena fatua which are major threats to wheat crop in Pakistan. Among the isolated metabolites, one compound was found active against the test weed species whose activity is reported in the present work. The chemical name of the compound is 2-(1, 4-dihydroxybutan-2-yl)-1, 3-dihydroxy-6, 8-dimethoxyanthracene-9, 10(4aH, 9aH)-dione with mass of 388. Results showed that all seeds germinated in control treatment; however, with the metabolite treated, the growth was retarded to different levels in all parts of the weeds. At a dose of 1000 μg/mL of the pure compound, 100% seeds of S. marianum and 60% seeds of A. fatua were inhibited. Interestingly, the pure compound exhibited less inhibition of 10% towards the seeds of common wheat (Triticum aestivum).

The soil microbial fuel cells (SMFCs) were constructed to remediate soils contaminated by polycyclic aromatic hydrocarbons (PAHs). With a maximum power density of 12.1mWm -2 and an internal resistance of 470Ω, a closed SMFC showed electricity generation comparable to that by an open SMFC after 175days of operation and meanwhile increased the removal rates of anthracene, phenanthrene, and pyrene to 54.2±2.7%, 42.6±1.9% and 27.0±2.1% from 20.8±1.1%, 17.3±1.2% and 11.7±0.9%, respectively, by the open SMFC. Both the electricity generation and the removal of PAHs increased with the decreased electrode interval. When the electrode interval ranged between 4cm and 10cm, the more closely the electrodes were positioned, the more efficient the electricity generation and removal of PAHs became. Dominated by the genus of Geobacter, the SMFC was enriched in electrogenic bacteria at the anode surface, and the growth of certain microbes other than electrogenic bacteria in the soil was improved by electrical stimulation. This finding reveals the critical mechanism underlying electricity generation and improved the removal of PAHs., (Copyright © 2017 Elsevier B.V. All rights reserved.)

Malaria is one of the three major global public health threats due to a wide spread resistance of the parasites to the standard antimalarial drugs. Considering this growing problem, the ethnomedicinal approach in the search for new antimalarial drugs from plant sources has proven to be more effective and inexpensive. The leaves of Aloe pulcherrima Gilbert and Sebsebe, an endemic Ethiopian plant, are locally used for the treatment of malaria and other infectious diseases. Application of the leaf latex of A. pulcherrima on preparative silica gel TLC led to the isolation of two C -glycosylated anthrones, identified as nataloin ( 1 ) and 7-hydroxyaloin ( 2 ) by spectroscopic techniques (UV, IR, ¹H- and 13 C-NMR, HR-ESIMS). Both the latex and isolated compounds displayed antimalarial activity in a dose-independent manner using a four-day suppressive test, with the highest percent suppression of 56.2% achieved at 200 mg/kg/day for 2 . The results indicate that both the leaf latex of A. pulcherrima and its two major constituents are endowed with antiplasmodial activities, which support the traditional use of the leaves of the plant for the treatment of malaria.

Four new dianthrone glycosides, named polygonumnolides C1-C4 (1-4), were isolated from the dried roots of Polygonum multiflorum Thunb, together with two known emodin dianthrones (5-6). Their hepatotoxicities were evaluated against L-02 cell lines. Compounds 1-4 showed weak hepatotoxicity against L-02 cell lines with IC50 values of 313.05, 205.20, 294.20, and 207.35 μM, respectively.

Three new anthraquinone secondary metabolites were isolated from Symplocos racemosa, a small tree of family symplocaceae. The structures of compounds (1-3) were elucidated to be 1,4-dihydroxy-6-(ethoxymethyl)-8-propylanthracene-9,10-dione (1), 1,4-dihydroxy-6-(hydroxymethyl)-8-butylanthracene-9,10-dione (2) and 1,4-dihydroxy-6-(hydroxymethyl)-8-propyl anthracene-9,10-dione (3) using their spectral data, i.e. through IR, UV, (1)H NMR, (13)C NMR and two-dimensional (2D) NMR techniques including heteronuclear multiple quantum coherence, heteronuclear multiple bond correlation and correlation spectroscopy.

We sought to compare the abilities of the specialist Lepidoptera Pyrrhopyge thericles (Hesperiidae) and the generalist Periphoba arcaei (Saturniidae) to assimilate three highly cytotoxic compounds from their larval host plant, Vismia baccifera (Clusiaceae) and to determine whether either insect discriminated in its assimilation of the compounds that are structurally similar but of variable cytotoxicity. Vismione B (1), deacetylvismione A (2), and deacetylvismione H (3) are cytotoxic compounds isolated from V. baccifera. Compound 1 was found in the 2nd and 3rd instars of P. arcaei, but not in the mature larvae or the pupae. Pyrrhopyge thericles assimilated trace quantities of compound 1 and deacetylvismione A (2), which were both found in the 3rd and 4th instars. In extracts of V. baccifera, compound 2 is present at levels approximately 6-fold greater than compound 1, indicating that the generalist P. arcaei is capable of selectively sequestering cytotoxic compounds from its host plant. Compounds 1 and 2 show comparable cytotoxicities in three different cancer cell lines, suggesting that properties other than cytotoxicity are responsible for the selective sequestration of 1 by P. arcaei. This study represents the first time that sequestration of this class of compounds has been recorded in the Lepidoptera.

The ethanolic extract of Aloe barbadensis Miller leaf skin showed inhibitory activity against phosphodiesterase-4D (PDE4D), which is a therapeutic target of inflammatory disease. Subsequent bioassay-guided fractionation led to the isolation of two new anthrones, 6'-O-acetyl-aloin B (9) and 6'-O-acetyl-aloin A (11), one new chromone, aloeresin K (8), together with thirteen known compounds. Their chemical structures were elucidated by spectroscopic methods including UV, IR, 1D and 2D NMR, and HRMS. All of the isolates were screened for their inhibitory activity against PDE4D using tritium-labeled adenosine 3',5'-cyclic monophosphate ((3)H-cAMP) as substrate. Compounds 13 and 14 were identified as PDE4D inhibitors, with their IC50 values of 9.25 and 4.42 μM, respectively. These achievements can provide evidences for the use of A. barbadensis leaf skin as functional feed additives for anti-inflammatory purpose., (Copyright © 2014 Elsevier B.V. All rights reserved.)

The first naturally occurring trimeric anthracene derivatives, stemphylanthranols A and B (1 and 2), were obtained from the endophytic fungus Stemphylium globuliferum that had been isolated from Juncus actus growing in Egypt. The structures of the new compounds were unambiguously determined by 1D and 2D NMR, and by HRMS. A hypothetical biosynthetic pathway for the new trimers is proposed.

As part of our program to identify novel secondary metabolites that target drug-resistant ovarian cancers, a screening of our aquatic-derived actinomycete fraction library against a cisplatin-resistant ovarian cancer cell line (OVCAR5) led to the isolation of novel diaza-anthracene antibiotic diazaquinomycin E (DAQE; 1), the isomeric mixture of diazaquinomycin F (DAQF; 2) and diazaquinomycin G (DAQG; 3), and known analog diazaquinomycin A (DAQA; 4). The structures of DAQF and DAQG were solved through deconvolution of X-Ray diffraction data of their corresponding co-crystal. DAQE and DAQA exhibited moderate LC50 values against OVCAR5 of 9.0 and 8.8 μM, respectively. At lethal concentrations of DAQA, evidence of DNA damage was observed via induction of apoptosis through cleaved-PARP. Herein, we will discuss the isolation, structure elucidation, and biological activity of these secondary metabolites.

Two new fungal pigments named schweinitzins A and B (1-2), together with (S)-torosachrysone-8-O-methyl ether (3) and emodin-6,8-di-O-methyl ether (4) have been isolated from the methanolic extract of the fruit bodies of Xylaria schweinitzii (Xylariaceae) collected in Cuc Phuong national park, Ninh Binh province, Vietnam, by silica gel column chromatography and preparative HPLC. Their structures were elucidated by spectroscopic analysis such as IR, UV-Vis, 2D NMR and FT-ICR-MS. In addition, two compounds (1 and 3) showed strong cytotoxicity against all four cancer cell lines, KB (a human epidermal carcinoma), MCF7 (human breast carcinoma), SK-LU-I (human lung carcinoma) and HepG2 (hepatocellular carcinoma).

Ethnopharmacological Relevance: Aquaporin-3 (AQP3) is expressed in mucosal epithelial cells in the colon and is important for regulating fecal water content. We examined the role of AQP3 in the laxative effect of rhubarb extract., Methods: After orally administering rhubarb extract or its major component (sennoside A) to rats, the fecal water content, AQP3 expression and prostaglandin E2 (PGE2) concentrations in the colon were examined. The mechanism by which sennoside A decreases the expression of AQP3 was examined using the human colon cancer HT-29 cells and macrophage-derived Raw264.7 cells., Results: During diarrhea by rhubarb extract administration, the PGE2 levels in the colon increased while the AQP3 expression significantly decreased. Similar changes were also observed when sennoside A was administered. When sennoside A or its metabolites, rheinanthrone and rhein were added to Raw264.7 cells, a significant increase in the PGE2 concentration was observed only in cells treated with rheinanthrone. Fifteen minutes after adding PGE2 to the HT-29 cells, the AQP3 expression decreased to approximately 40% of the control. When pretreated with indomethacin, sennoside A neither decreased the AQP3 expression nor induced diarrhea., Conclusions: Sennoside A may decrease AQP3 expression in the colon to inhibit water transport from the luminal to the vascular side, leading to a laxative effect. The decreases in the levels of AQP3 are caused by rheinanthrone, which is a metabolite of sennoside A, this metabolite activates the macrophages in the colon and increases the secretion of PGE2; PGE2 acts as a paracrine factor and decreases AQP3 expression in colon mucosal epithelial cells., (Copyright © 2014 Elsevier Ireland Ltd. All rights reserved.)

7-O-methylvariecolortide A (1), variecolortide B (2), and variecolortide C (3), the rare variecolortides existing in racemic manner, were isolated from an endolichenic fungal strain Eurotium sp. (No. 17-11-8-1). With the chiral HPLC technology, (-)-(S)-7-O-methylvariecolortide A (1a), (+)-(R)-7-O-methylvariecolortide A (1b), (-)-(S)-variecolortide B (2a), (+)-(R)-variecolortide B (2b), (-)-(S)-variecolortide C (3a), and (+)-(R)-variecolortide C (3b) were successfully separated and obtained. Their absolute configurations were firstly assigned by ECD experiment and ECD calculation. According to the relation of isolated compounds, a plausible biosynthetic pathway for variecolortides was proposed. In caspase-3 enzymatic assay, compounds 1-3 showed inhibitory activity, with IC50 values of 1.7, 0.8 and 15.7 μM, respectively., (Copyright © 2013 Elsevier B.V. All rights reserved.)

Water disinfection technologies based on ultraviolet (UV) radiations emitted by Light-Emitting Diodes (LED), as a wastewater tertiary treatment, have been shown to be promising for water reuse. Here, we assessed the fate of two ubiquitous pollutants, carbamazepine and anthracene, in soil watered with either UV-LED treated wastewaters or irrigation water. After 3 months, anthracene and carbamazepine were transformed two and three times faster respectively, in soils watered with UV-LED wastewater than in soils watered with tap water (probably because of the addition of organic matter by the effluent). Laccase activity was induced in the presence of the pollutants and anthraquinone was found as anthracene product of oxidation by laccases. Moreover, the addition of these pollutants into soil did not affect the functional diversity of autochthonous microbial communities assessed by Ecolog plates. Cellulase, protease and urease activities increased in soils watered with UV-LED treated wastewaters (UV-LED WW), showing transformation of organic matter from the effluent and lipase activity increased by anthracene addition, confirming the potential role of these enzymes as indicators of hydrocarbon contamination., (Copyright © 2013 Elsevier Ltd. All rights reserved.)

Two bisdihydroanthracenone atropodiastereomeric pairs, including homodimeric flavomannin A (1) and the previously unreported flavomannin B (2), two new unsymmetrical dimers (3 and 4), and two new mixed dihydroanthracenone/anthraquinone dimers (5 and 6) were isolated from Talaromyces wortmannii , an endophyte of Aloe vera . The structures of 2-6 were elucidated by extensive NMR and mass spectrometric analyses. The axial chirality of the biaryls was determined using TDDFT ECD and VCD calculations, the combination of which however did not allow the assignment of the central chirality elements of 1. The compounds exhibited antibacterial activity against Staphylococcus aureus , including (multi)drug-resistant clinical isolates. Reporter gene analyses indicated induction of the SOS response for some of the derivatives, suggesting interference with DNA structure or metabolism. Fluorescence microscopy demonstrated defective segregation of the bacterial chromosome and DNA degradation. Notably, the compounds showed no cytotoxic activity, encouraging their further evaluation as potential starting points for antibacterial drug development.

We demonstrate a new method for the fabrication of free-standing mats of mesoporous ZnO nanofibers by electrospinning a blend of zinc acetate with a carrier polymer, polyacrylonitrile (PAN) in N,N-dimethyl-formamide (DMF) solvent. Decomposition of PAN by calcination produces porous ZnO nanofibers with fiber diameters in the range of 50-150 nm depending on the electrospinning conditions such as the precursor solution concentration, electric field strength, and solution flow rate. The fibers are characterized for their morphology, phase composition, band gap, crystallinity, surface area, and porosity. In this paper, optimized mats of ZnO nanofibers with an average fiber diameter of 60 nm are shown to be highly effective in the photocatalytic degradation of the PAH dyes--naphthalene and anthracene. Nanofiber mats fabricated here may also find applications in gas sensing, piezoelectric devices, optoelectronics, and photocatalysis., (Copyright © 2012 Elsevier Inc. All rights reserved.)

Anthracene, among the 16 US EPA polycyclic aromatic hydrocarbons (PAHs), is a typical low molecular weight environmental contaminant, which gains concern on its biodegradation under hypersaline condition. In this study, an anthracene-degrading bacterial strain was isolated from highly saline petroleum-contaminated soil. Based on its physiological, biochemical characteristics and 16S rDNA sequence analysis, the bacteria was preliminary identified and named as Martelella sp. AD-3. The strain was able to utilize anthracene as sole carbon source for growth and the degradation occurred under broad salinities (0.1% to 10%) and varying pHs (6.0 to 10.0). The optimized degradation conditions were initial concentration 25 mg x L(-1), culture temperature 30 degrees C, pH 9.0 and salinity 3%. And 94.6% of anthracene was degraded by strain AD-3 under the optimal conditions within 6 days. Degenerate primers design was performed with a reported dioxygenase alpha subunit homologous gene. A length of 307 bp fragment of the partial dioxygenase gene sequences (GenBank accession: JF823991.1) was amplified by nested PCR. The clones amino acid sequence from strain AD-3 showed 95% identity to that of the partial naphthalene dioxygenase large-subunit from Marinobacter sp. NCE312 (AF295033). The results lay a foundation for the further study of molecular mechanism involved in the PAHs biodegradation by strain AD-3.

Despite the increasing agricultural use of biochar as a way of combining the utilization of biomass for energy production with the removal of CO(2) from the atmosphere, it is not known how variations in pyrolysis temperature and feedstock type affect concentration and composition of polycyclic aromatic hydrocarbons (PAHs) that inevitably form and associate with biochar. To close this knowledge gap, we quantified 11 unsubstituted three- to five-ring PAHs as well as alkylated forms of phenanthrene and anthracene in grass and wood chars produced in 100 °C increments across a temperature range (100 to 700 °C). Our results show that solvent-extractable PAH concentrations in biochars produced at heat treatment temperatures (HTTs) of 400 and 500 °C greatly exceed those observed at higher and lower temperature, supporting a low HTT solid-phase formation mechanism operable at temperatures commonly used for industrial biochar production. The maximum extractable yield of 'pyrolytic' unsubstituted PAHs for grass (22 μg g(-1) at HTT = 500 °C) greatly exceeds the value for wood (5.9 μg g(-1)). Moreover, PAH signatures (e.g., total monomethylphenanthrene to phenanthrene ratios, MP/P ~2-3) at intermediate temperatures (400 °C) resemble those of fossil oils rather than that commonly attributed to pyrolytic products. Further research is needed to characterize the PAH evolution in modern pyrolysis reactors and assess the fate of biochar-bound PAHs in soils and sediments. Various commonly applied PAH ratios and indicator compounds show promise as markers for specific feedstock materials and pyrolysis conditions of biochars in environmental systems.

The nonnative hemlock woolly adelgid (Adelges tsugae Annand, Hemiptera: Sternorrhyncha: Adelgidae) has been a significant mortality agent of eastern hemlock (Tsuga canadensis Carriere) throughout a large portion of its geographic range. During a study investigating adelgid vigor in relation to host health, it was noted that adelgid extracts ranged from a yellow to a deep red color. Analysis by GC-MS identified the presence of the anthraquinone, chrysophanol and its anthrone precursor, chrysarobin in the extract. These compounds are predator deterrents in several other insects, including chrysomelid beetles. It is hypothesized that these compounds serve a similar purpose in the hemlock woolly adelgid.

A galactose- and N-acetyl-D-galactosamine-specific lectin (Viscum album L. var. coloratum agglutinin, VCA), which is known for its anticancer activity, was isolated from mistletoe. In this study, we investigated the antimutagenic potentials of VCA by using the pre-incubation method of the Ames test (Salmonella typhimurium TA98 and TA100) in the presence or absence of S9 mixture. Viscum album L. var. coloratum agglutinin was assessed for its antimutagenic properties against the mutagens 2-aminoanthracene (2AA) and furylfuramide (AF-2) for strain TA98, and sodium azide (NaN(3) ) and 2-aminoanthracene (2AA) for strain TA100. The concentrations used for this test compound were 100, 200 and 400 µg per plate.  Viscum album L. var. coloratum agglutinin showed moderate, but not negligible, protective effects regarding the antimutagenic properties against the direct-acting mutagens NaN(3) and AF-2. Furthermore, VCA was more effective in preventing the mutagenicity of the indirect-acting mutagen 2-AA (in the presence of S9) when tested with both TA98 and TA100. In conclusion, this report has shown broad ranging antimutagenic effects of VCA to numerous mutagens in TA98 and TA100 Salmonella typhimurium strains. Although the data presented here cannot be applied in vivo, they can support other antimutagenic and anticarcinogenic findings for VCA., (Copyright © 2011 John Wiley & Sons, Ltd.)

In the search for new antimicrobial and antioxidant compounds from plants, the latex of the medicinal plant Aloe harlana Reynolds from Ethiopia was subjected to bioassay-guided fractionation, which led to the isolation of two known compounds, anthrone (aloin) and chromone (7-O-methylaloeresin A). The latex and its two constituents were assessed for their possible antimicrobial activities against 23 bacterial and four fungal strains using the disc diffusion method and their antioxidant activity by two complementary test systems, namely 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2-deoxyribose degradation assay methods. The isolated compounds showed promising results against various pathogenic bacterial and fungal strains in comparison with standard drugs. Moreover, 7-O-methylaloeresin A exhibited good activity against multiple drug resistant Staphylococcus aureus (NCTC 11994) and Salmonella typhimurium (ATCC 1255) with MIC values of 0.72 and 0.18 mm, respectively. Among the fungal strains tested, Candida albicans (ATCC 10231) was the most susceptible organism to the latex and the two isolated compounds. The latex and isolated compounds also showed significant activities on both antioxidant assays with the highest activity being observed for 7-O-methylaloeresin A, which gave IC(50) values of 0.026 mm and 0.021 mm for DPPH and 2-deoxyribose degradation assay, respectively. These findings support the traditional uses of the plant for the treatment of various infectious and inflammatory diseases., (Copyright © 2011 John Wiley & Sons, Ltd.)

A new cyclohexadepsipeptide, conoideocrellide A (1), its linear derivatives, conoideocrellides B-D (2-4), three new hopane triterpenoids (5-7), two new bioxanthracenes (9 and 10), and a new isocoumarin glycoside (13) were isolated from the scale insect pathogenic fungus Conoideocrella tenuis BCC 18627. Biological activities of the new compounds were evaluated.

The Japanese mealybug, Planococcus kraunhiae, is suitable as a model insect for biosynthetic studies on mealybug pigments. Four yellow pigments, including two novel ones, were isolated from the mealybug bodies and characterized as endocrocin, a dicarboxylic acid named fujikonaic acid (1), emodin 1-O-β-D-glucopyranoside and 7-hydroxyemodin 1-O-β-D-glucopyranoside (2). The enzymatic activity of emodin 1-O-glucosyltransferase was observed in the extracts of insect bodies.

A new anthracene derivative, 3-hydroxy-1-keto-3-methyl-8-methoxy-1,2,3, 4-tetrahydro-benz[α]anthracene, was isolated from the marine strain Streptomyces sp. W007, and its structure was established by spectroscopic analysis including mass spectra, 1D- and 2D-NMR ((1)H-(1)H COSY, HMBC, HSQC and NOESY) experiments. 3-hydroxy-1-keto-3-methyl-8-methoxy-1,2,3,4-tetrahydro-benz[α]anthracene showed cytotoxicity against human lung adenocarcinoma cell line A549.

Six C-glucosyl anthrones were characterized as three pairs of epimers by on-line high performance liquid chromatography-circular dichroism (HPLC-CD) analysis and isolated from the roots of Rumex dentatus by column chromatography. Their structures were elucidated by mass spectrometry, nuclear magnetic spectroscopy and HPLC-CD analysis. They are 10R-C-beta-D-glucosyl-10-hydroxyemodin-9-anthrone (rumejaposide E, 1) and 10S-C-beta-D-glucosyl-10-hydroxyemodin-9-anthrone (rumejaposide F, 2), 10R-C-beta-D-glucosylemodin-9-anthrone (rumejaposide G, 3) and 10S-C-beta-D-glucosylemodin-9-anthrone (rumejaposide H, 4), 10S-C-beta-D-glucosyl-10-hydroxychrysophanol-9-anthrone (cassialoin, 5) and 10R-C-beta-D-glucosyl-10-hydroxychrysophanol-9-anthrone (rumejaposide I, 6). Rumejaposides F-I (2-4 and 6) were new C-glucosyl anthrones. Rumejaposide E (1) and cassialoin (5) were isolated for the first time in Rumex plants. On-line HPLC-UV-CD analysis was a useful tool for structure elucidating epimeric C-glycosides anthrones 3-6 because of the poor stability of the pure isomers (3 and 4) and the minute quantity of 5 and 6 in the mixture., (2010 Elsevier B.V. All rights reserved.)

The template-directed synthesis of a bistable donor-acceptor [2]catenane wherein both translational isomers--one in which a tetrathiafulvalene unit in a mechanically interlocked crown ether occupies the cavity of a cyclobis(paraquat-p-phenylene) ring and the other in which a 1,5-dioxynaphthalene unit in the crown ether resides inside the cavity of the tetracationic cyclophane--exist in equilibrium in solution, has led to the isolation and separation by hand picking of single crystals colored red and green, respectively. These two crystalline co-conformations have been characterized separately at both the molecular and supramolecular levels, and also by dynamic NMR spectroscopy in solution where there is compelling evidence that the mechanically interlocked molecules are present as a complex mixture of translational, configurational, and conformational isomers wherein the isomerization is best described as being a highly dynamic and adaptable phenomenon.

Three new C-glucosylanthrones, 3'-O-acetyl-5-hydroxylaloin A (2), 2',6'-O-diacetyl-5-hydroxylaloin A (4), and 4',6'-O-diacetyl-5-hydroxylaloin A (5), along with three known compounds, 5-hydroxyaloin A (1), 6'-acetyl-5-hydroxylaloin A (3), and 4-methoxy-6-(2',4'-dihydroxy-6'-methylphenyl)-pyran-2-one (6), were isolated from the leaves of Aloe nobilis, and their structures were elucidated on the basis of spectroscopic evidences. Compounds 1, 2, 4 and 5 showed antioxidant activity with inhibitory rates of 31.0, 34.0, 34.0, and 42.0%, respectively, at 10(-5) M.

Chrysophanol, physcion, emodin, floribundone-1, 5,7'-physcion-fallacinol, and the novel 5,7'-physcion-physcion-10'-C-alpha-arabinopyranoside were isolated from the stem bark of Senna septemtrionalis. The structures of these secondary metabolites were determined on the basis of spectroscopic analysis, especially from NMR spectra in conjunction with COSY, HMQC, HMBC and TOCSY.

Two highly water-soluble amino acids, which derived from beta-CDs, i.e., glutamic acid-beta-cyclodextrin (GluCD) and ethylene-diamine-beta-cyclodextrin (EDCD), were synthesized and were examined for their effect on solubilization of anthracene (ANT), complexation of cadmium (Cd2+), and elution removal of ANT and Cd2+ in soil. The results showed that GluCD and EDCD were powerful complexant for ANT and Cd2+. In the presence of 10 g/L GluCD and EDCD, the solubilization of ANT increased by 47.04 and 23.85 times compared to the control, respectively. GluCD resulted in approximately 90% complexation of Cd2+ while 70% complexation was observed for EDCD. Simultaneously, GluCD and EDCD could greatly enhance the elution removal of ANT and Cd2+ from soil. GluCD resulted in the highest elution efficiency of ANT and Cd2+. With the addition of 10 g/L GluCD, 53.5% of ANT and 85.6% of Cd2+ were eluted, respectively. The ANT had a negligible effect on the Cd2+ removal due to different complexing sites of ANT and Cd2+, while Cd2+ enhanced the ANT removal under the addition of GluCD because Cd2+ neutralized the -COOH group of GluCD. Adversely, the removal of ANT was decreased with Cd2+ under the addition of EDCD, this was due to the fact that Cd2+ enhanced the polarity of EDCD molecule and inhibited the complexation between ANT and EDCD. The study suggested that GluCD could be preferred and be successfully applied to remediation of heavy metals or organic compounds in contaminated soil.

Several studies have been performed reporting antitumoral activity of different mushroom extracts. The current study reports the antiproliferative activity of flavomannin-6,6'-dimethylether obtained from a very common edible mushroom: Tricholoma equestre(L.)P.Kumm, and the characterization of its effects at molecular level. Concentrations causing 50% and 80% growth inhibition on human adenocarcinoma colorectal Caco-2 cells were determined (in microg/mL: IC(50)=96+/-3 after 24 h and 78+/-7 after 48 h, IC(80)=112+/-4 after 24 h and 90+/-3 after 48 h) by using MTT method. It was demonstrated that flavomannin-6,6'-dimethylether induced an arrest in G0/G1 phase of the cell cycle by flow cytometry analysis and an increase of p27 protein level by Western blot. Furthermore, this compound did not induce apoptosis by flow cytometry or DNA fragmentation by gel electrophoresis. Thus, it could be a promising agent due to its cytostatic effect against Caco-2 tumoral cells, and the absence of a genotoxic effect.

Fabrication of porous frits to retain stationary phases is a critical issue in column preparation for capillary electrochromatography (CEC). In this work, porous frits were prepared by applying an external magnetic field to magnetically responsive particles placed inside a fused-silica capillary. Three batches of uniform magnetite spheres with particle diameters of 0.3, 0.4, and 0.6 microm and saturation magnetization values of 73.03, 74.41, and 77.83 emu/g, respectively, were used as frit particles and octadecyl- and phenyl-bonded silica gels were packed successfully into frit-containing capillaries. The performance of the resulting magnetically immobilized frits and packed columns was evaluated. The electroosmotic mobilities in capillaries containing outlet frit only were found to be reduced by 2-4% whereas the plate heights of an unretained marker increased by 30-50% as compared to those in open capillaries. These variations are believed to be associated with the inhomogeneities of the packed structure of the frits. The magnetically immobilized frits showed adequate mechanical strength to withstand the flow drag force, allowing separation in capillaries packed with 5-mum stationary phases up to 10-15 cm, thus rendering column efficiency and reproducibility comparable with those obtained with sintered frits. Taken together, retaining frits made of uniform magnetite particles serves as a viable alternative to sintered frits for column preparation, which offers several distinct advantages such as ease of preparation, improved durability as compared to sintered frits where the removal of the polyimide coating makes the packed column susceptible to breakage, and use of large-bore capillaries for semipreparative separations.

There is considerable interest in the isolation of potent radical scavenging compounds from natural resources to treat diseases involving oxidative stress. In this report, four new fungal metabolites including one new bisdihydroanthracenone derivative (1, eurorubrin), two new seco-anthraquinone derivatives [3, 2-O-methyl-9-dehydroxyeurotinone and 4, 2-Omethyl- 4-O-(alpha-D-ribofuranosyl)-9-dehydroxyeurotinone], and one new anthraquinone glycoside [6, 3-O-(alpha-D-ribofuranosyl)- questin], were isolated and identified from Eurotium rubrum, an endophytic fungal strain that was isolated from the inner tissue of the stem of the marine mangrove plant Hibiscus tiliaceus. In addition, three known compounds including asperflavin (2), 2-O-methyleurotinone (5), and questin (7) were also isolated and identified. Their structures were elucidated on the basis of spectroscopic analysis. All of the isolated compounds were evaluated for 1,1-diphenyl-2-picrylhydrazyl(DPPH) radical scavenging activity.

Recycling of municipal wastewater requires treatment with flocculants, such as polyacrylamide. It is unknown how polyacrylamide in sludge affects removal of polycyclic aromatic hydrocarbons (PAH) from soil. An alkaline-saline soil and an agricultural soil were contaminated with phenanthrene and anthracene. Sludge with or without polyacrylamide was added while emission of CO(2) and concentrations of NH(4)(+), NO(3)(-), NO(2)(-), phenanthrene and anthracene were monitored in an aerobic incubation experiment. Polyacrylamide in the sludge had no effect on the production of CO(2), but it reduced the concentration of NH(4)(+), increased the concentration of NO(3)(-) in the Acolman soil and NO(2)(-) in the Texcoco soil, and increased N mineralization compared to the soil amended with sludge without polyacrylamide. After 112d, polyacrylamide accelerated the removal of anthracene from both soils and that of phenanthrene in the Acolman soil. It was found that polyacrylamide accelerated removal of phenanthrene and anthracene from soil.

Two new anthracene glycosides (1, 2) were isolated from aerial parts of Rhodomyrtus tomentosa, along with three known compounds (3-5). The structures of two new compounds were established to be 4,8,9,10-tetrahydroxy-2,3,7-trimethoxyanthracene-6-O-beta-D-glucopyranoside (1) and 2,4,7,8,9,10-hexahydroxy-3-methoxyanthracene-6-O-alpha-L-rhamnopyranoside (2) based on spectroscopic and chemical methods. Among them, compound 1, 2, and 5 significantly (P<0.05) increased the alkaline phosphatase activity, collagen synthesis, and mineralization of the nodules of MC3T3-E1 osteoblastic cells compared to those of the control, respectively.

In a previous study, remediation of anthracene from soil was faster in the top 0-2 cm layer than in the lower soil layers. It was not clear whether this faster decrease was due to biotic or abiotic processes. Anthracene-contaminated soil columns were covered with black or transparent perforated polyethylene so that aeration occurred but that fluctuations in water content were minimal and light could reach (LIGHT treatment) or not reach the soil surface (DARK treatment), or left uncovered so that soil water content fluctuate and light reached the soil surface (OPEN treatment). The amount of anthracene, microbial biomass C, and microbial activity as reflected by the amount of CO(2) produced within 3 days were determined in the 0-2 cm, 2-8 cm, and 8-15 cm layer after 0, 3, 7, 14, and 28 days. In the 0-2 cm layer of the OPEN treatment, 17% anthracene remained, 48% in the LIGHT treatment and 61% in the DARK treatment after 28 days. In the 2-8 cm and 8-15 cm layer, treatment had no significant effect on the dissipation of anthracene from soil after 14 and 28 days. It was found that light and fluctuations in water content stimulated the removal of anthracene from the top 0-2 cm soil layer, but not from the lower soil layers. It can be speculated that covering contaminated soil or piling it up will inhibit the dissipation of the contaminant.

A phytochemical study of the stem bark of Vismia laurentii resulted in the isolation of a tetracyclic triterpene, tirucalla-7,24-dien-3-one (1), and seven other known compounds: 3-geranyloxyemodin (2), vismiaquinone A (3), vismiaquinone B (4), bivismiaquinone (5), epifriedelinol (6), betulinic acid (7) and stigmasta-7,22-dien-3-ol (8). The structure of all these compounds was elucidated by spectroscopic means. The stem bark extract and compounds 1 and 3 showed good antimalarial activity against the W2 strain of Plasmodium falciparum.

Aloe arborescens plants, originating from the deserts of South Africa, are grown in the Introduction Garden at Sede Boker in the Negev Desert of Israel. In previous studies, we developed agro-technical methods to raise the content of secondary phenol metabolites (SPhMs) in the Aloe leaves. Plants that are subjected to repeated leaf pruning respond by increasing the content of their SPhMs. The SPhMs found in Aloe arborescens include barbaloin, aloenin and derivatives of aloeresin. Such compounds are used for many purposes, including human skin protection from sun and fire burns and high radiation, as products of the pharmaceutics and cosmetics industries, and as food supplements for treating stomach ulcers and diabetes. In the current study, the SPhMs were separated from pruned leaves of the same A. arborescens plants at the same time by two methods: (1) exudation by squeezing the tissues of the leaves, (2) immersion of the leaves' pruned cut bottom in water and collection of the extract. The exudates and extract were frozen, freeze-dried to a powder and the SPhMs were then separated by chromatography. The yield of powder from water extraction from pruned leaves was much lower than the yield from the exudates. However, higher percentages of the powder from the water extraction contained SPhMs (between 80 and 92.7%). The content of powder in leaf exudates from pruned leaves was much higher because the SPhMs were squeezed out from the cells and tissues. However, the percentages of SPhMs in this powder were much lower (between 39 and 62%).