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PubMed1988

Determination of trace organic compounds in effluents from a coal-fired power plant.

Solid and gaseous emissions from a power plant fired with South African coal and maintained at full load (320 MWe) were characterized for their composition in polynuclear aromatic hydrocarbons (PAH) and n-alkanes (n-A). 25 n-A (from C12 to C36) and 34 PAH (from naphthalene to coronene) were determined by gas chromatography/mass spectrometry. Samples were collected in different points of the plant: the bottom hopper of the boiler, the electrostatic precipitator (ESP) hopper and the ductwork system before and after the ESP. The pulverized coal was also analysed by the same procedure in order to find any correlation with the composition of emissions. PAH concentration profiles of the coal and the combustion products, which will be useful for evaluation of environmental impact, were obtained.

Air Pollutants, Occupational↗
PubMed1992

Arctic contaminants: sources, occurrence and pathways.

Potentially toxic organic compounds, acids, metals and radionuclides in the northern polar region are a matter of concern as it becomes evident that long-range transport of pollution on hemispheric to global scales is damaging this part of the world. In this review and assessment of sources, occurrence, history and pathways of these substances in the north, the state of knowledge of the transport media--the ocean and atmospheric circulation--is also examined. A five-compartment model of the northern region is developed with the intent of assessing the pathways of northern contaminants. It shows that we know most about pathways of acids, metals and radionuclides and least about those of complex synthetic organic compounds. Of the total annual inputs of anthropogenic acidic sulphur and the metals lead and cadmium to the Arctic via the atmosphere, an estimated 10-14% are deposited. A water mass budget for the surface layer of the Arctic Ocean, the most biologically active part of that sea, is constructed to examine the mass budget for one of the major persistent organochlorine compound groups found in remote regions, hexachlorocyclohexanes (HCH), one isomer of which is lindane. It is concluded that both the atmosphere and the ocean are important transport media. Even for the HCH substances which are relatively easily measured and simple in composition compared to other synthetic organics, we know little about the occurrence and environmental physical/chemical characteristics that determine pathways into the food chain. More environmental measurements, chemical characterization studies and environmental chemical transport modelling are needed, as is better knowledge of the circulation of the Arctic Ocean and the marine food web.

Acids↗
PubMed2005

Schisandrin B--a novel inhibitor of P-glycoprotein.

P-glycoprotein-mediated drug efflux is one of the major causes of the cancer multidrug resistance (MDR). Inhibition of P-glycoprotein could reverse cancer MDR. Here, we show that schisandrin B, a naturally occurring compound from Schisandra chinensis (Turcz.) Baill, bears strong potency to inhibit P-glycoprotein. Schisandrin B reversed the drug resistance of four MDR cell lines characterized with overexpression of P-glycoprotein and fully restored the intracellular drug accumulation by interacting with P-glycoprotein. Schisandrin B has a core structure of dibenzocyclooctadiene, representing a novel P-glycoprotein inhibitor. To our best knowledge, the role of schisandrin B to inhibit P-glycoprotein has not been reported.

ATP Binding Cassette Transporter, Subfamily B↗
PubMed1997

Chemical characterization of the PM10 fraction of airborne particulate matter in the urban atmosphere.

This study examines the chemical composition of PM10, the thoracic fraction of atmospheric particulate matter. This fraction is characterized by a very complex composition and is able to penetrate the human organism corresponding to a "cut point" at the level of the larynx. We used a sampling device to separate the PM10 from other fractions with different aerodynamic behavior. The high volume sampler collected large amounts of material, making it easier to study the micropollutants. Furthermore, it met EPA performance specifications for the measurement of suspended PM10 fraction. We collected the samples during different metereological conditions in the urban area of the town of Leghorn in Tuscany, Italy. Two sites, characterized by different settings, were chosen in the city. Both sites were marked by intense motor vehicle traffic. A better chemical characterization of the collected material became possible using different analytical techniques. The use of large-size cellulose or glass fiber filters allowed us to subdivide the sample and to submit each portion to a different investigative technique. The PAH content of the PM10 fraction was examined, particularly for those compounds of toxicological interest. The concentrations of the compounds were evaluated by HPLC with diode array UV detection. We further determined the contents of various heavy metals from anthropic or telluric sources (Pb, Cu, Fe, Cr, Cd, Mn, V, and Ni) by means of an HGA Graphite Furnace AAS-Zeeman-Effect technique or AA-Flame spectrophotometry. The results of our experiment show that motor vehicle traffic is the prevailing pollution source. The metereological conditions also play a significant role. The samples taken closer to the industrial area of the town showed a slightly higher mean content of PM10 fraction. The concentrations of both heavy metals and PM10 were lower compared with equivalent data from other European cities.

Air Pollutants↗
PubMed1994

Pathology and toxicology of beluga whales from the St. Lawrence Estuary, Quebec, Canada. Past, present and future.

An indigenous population of 450-500 beluga whales (Delphinapterus leucas) inhabiting the St. Lawrence Estuary has been exposed chronically for more than 50 years to a complex mixture of industrial pollutants including organochlorinated compounds (OC), polycyclic aromatic hydrocarbons (PAH) and heavy metals. From 1983 to 1990, we have necropsied 45 well preserved carcasses out of a total of 120 beluga whales reported dead over this period. Of these 45 animals, nine were affected by 10 malignant neoplasms. Fifteen animals (33%) were affected by pneumonia. Milk production was compromised in eight of 17 mature females (41%), by inflammatory changes (seven animals) and cancer (one animal) which affected the mammary glands. Opportunistic bacteria were found in pure culture, and/or in significant amounts in at least two organs in 20 belugas (44%). The concentrations of both total PCBs and highly chlorinated PCB congeners were much higher in St. Lawrence animals than in Arctic beluga whales. OC-induced immunosuppression has been repeatedly demonstrated in a wide variety of animal species. Therefore, it is probable that the immune functions of St. Lawrence beluga whales are impaired. Benzo[a]pyrene adducts were detected in 10 of the 11 St. Lawrence beluga whales of which tissues (six livers, 10/11 brains) were analyzed by a method based on HPLC. No such adducts were found in four Arctic animals. Since benzo[alpha]pyrene is one of the most potent chemical carcinogens known to man, these compounds might be responsible for some of the cancers observed in that population. Overall, our findings contrast vividly with those of others who found that cancers are exceedingly rare in free-ranging odontocete populations and that the major causes for mortalities in these populations are bacteria, parasites, and trauma.

Animals↗
PubMed2004

Application of multi-way models to the time-resolved fluorescence of polycyclic aromatic hydrocarbons mixtures in water.

The time-resolved laser-induced fluorescence of a series of polycyclic aromatic compounds (PAHs) and mixtures of these latter in aqueous solution was measured by means of an apparatus equipped with optical fibers, which allows their real time in situ monitoring. The potential of such spectroscopic technique, yielding 4-way fluorescence data arrays, together with the application of multi-way models to the matricized data, was tested for the resolution of complex aqueous mixtures containing low concentrations of PAHs, as typical fluorescent pollutants in aquatic systems. PARAllel FACtors analysis was employed for the qualitative resolution of PAHs mixtures and for calculating the fluorescence lifetimes of single PAHs; n-way partial least squares analysis was applied for evaluating the concentration of the single PAHs in the aqueous mixtures.

Environmental Monitoring↗
PubMed2001

Resolution of GC-MS data of complex PAC mixtures and regression modeling of mutagenicity by PLS.

The present work describes a strategy to predict the mutagenicity of very complex mixtures of polycyclic aromatic compounds (PAC) from gas chromatography-mass spectrometry (GC-MS) patterns of the mixtures, each containing 260 compounds on average. The mixtures, 13 organic extracts of exhaust particles, were characterized by full scan GC-MS. The data were resolved into peaks and spectra for individual compounds by an automated curve resolution procedure. Similarity between spectra was evaluated for peaks that appeared within a time interval of 4 min, using a similarity index of 0.8 to ascertain that the same compound was represented by the same variable name (retention time) in all samples. The resolved chromatograms were integrated, resulting in a predictor matrix of size 13 x 721, which was used as input to a multivariate regression model. Partial least-squares projections to latent structures (PLS) were used to correlate the GC-MS chromatograms to mutagenicity as measured in the Ames Salmonella assay. The best model (high r2 and Q2) was obtained with 52 variables. These variables covary with the observed mutagenicity, and may subsequently be identified chemically. Furthermore, the regression model can be used to predict mutagenicity from GC-MS chromatograms of other organic extracts.

Air Pollutants↗
PubMed2005

Donor-acceptor-promoted gelation of polyaromatic compounds.

Low molecular mass organogels are nonconventional polymeric structures in which a minute amount of low molecular weight compound can reversibly gelify the whole solution without forming covalent bonds between the monomers. In this article, we demonstrate that certain electron acceptors (taking dinitrobenzoates as model compounds) that are incapable of gelifying the solvent on their own can assemble as much as a 15-16-fold larger amount of polyaromatic hydrocarbons (PAHs) and form two-component donor-acceptor organogels in different solvents. At the core of the long-range order stand donor-acceptor pairs. We assess our claims by detailed 1H NMR, spectrophotometry, fluorescence, and time-resolved fluorescence methods. The thermodynamics of the gelation process is described on the basis of temperature dependent 1H NMR studies. We believe that, in this case, 1H NMR provides direct quantification of the dissolved concentrations of the different species and therefore provides a direct way to measure the enthalpy, entropy, and free energy associated with gel formation.

Cyclization↗
PubMed1997

Chemical analysis and biological activity of airborne particulate matter.

We examined the chemical composition of the suspended particulate matter in a typical, middle-sized, nonindustrial Italian town in terms of total carcinogenic PAH, heavy metal, and polynuclear azo-aromatic compounds. The chemical data relate to the biological activity of the organic extract of the particulate matter (mutagenicity and mice alveolar macrophage phagocytosis inhibition). The concentration values of benz(a)pyrene, the concentration ratios of selected PAH's, and the GC-MS profile of some typical samples indicate that motor vehicle traffic is the main pollution source. PAH concentration is significantly correlated with mutagenicity and a phagocytosis inhibition of up to 75% was observed at the highest PAH concentration. As far as the effect of meteorological variables on PAH concentration and mutagen-icity is concerned, a statistically significant inverse correlation with temperature was found.

Air Pollutants↗
PubMed1997

Sister chromatid exchange induction in peripheral blood lymphocytes of traffic police workers.

Traffic police workers, as a population exposed to urban atmosphere, were compared with a control population exposed to indoor air pollution levels. Sister chromatid exchanges (SCEs) as a biomarker of effect were measured in peripheral blood lymphocytes of 54 exposed subjects and 35 controls, and environmental concentration of polynuclear aromatic hydrocarbon (PAH) tracer compounds was detected by personal air samplers. The mean exposure level to benzo[a]pyrene in our group of traffic policemen (3.4 mg/m3) was in the range that has been estimated in urban areas in Europe during the last 10 years. No difference in SCE levels was found between exposed workers (7.36, SD 1.35) and controls (7.47, SD 1.28). No correlation was observed between SCE/cell and airborne PAH concentration in the traffic worker population. A positive regression of SCE on exposure estimate was found only in the non-smoking group of police workers. Our findings suggest that exposure to urban air pollution does not induce relevant cytogenetic effects.

Adult↗
PubMed1991

Effect of dibenzo[a,c]cyclooctene lignans isolated from Fructus schizandrae on lipid peroxidation and anti-oxidative enzyme activity.

The effect of nine dibenzo[a,c]cyclooctene lignans isolated from Fructus schizandrae on in vitro and in vivo lipid peroxidation of liver microsomes as well as on anti-oxidative enzyme activities were studied. Seven of the nine lignans (1 mM) were shown to inhibit Vit C/NADPH induced lipid peroxidation (malondialdehyde (MDA) formation) of rat liver microsomes. Of these compounds, schisanhenol (Sal), S(-)schizandrin C (S(-)sin C) and S(-)schizandrin B (S(-)sin B) were shown to be more potent than Vit E at the same concentration. Sal and Sin B were able to inhibit gossypol-induced superoxide anion generation in rat liver microsomes. In addition, oral administration of Sal and Sin B markedly reduced liver MDA formation induced by ethanol, 15 ml/kg in mice, and increased superoxide dismutase and catalase activities in rat liver cytosol. The data of this paper are in favor of the conclusion that some lignans, like Sal, have strong anti-oxidant activity. The mechanisms of anti-oxidant activity of the lignans were discussed.

Animals↗
PubMed1989

Changes in the polynuclear aromatic hydrocarbon content of wheat grain and pasture grassland over the last century from one site in the U.K.

Crops harvested and stored from two long-term agricultural experiments started in the 1840-1850s at Rothamsted Experimental Station (U.K.) have been analyzed for polynuclear aromatic hydrocarbons (PAHs) because PAHs have increased four-to-five fold in the underlying 0-23 cm depth of soil over the last century due to atmospheric deposition. Bulked samples of herbage and wheat grain were analyzed for 16 compounds by gas chromatography-mass spectrometry for groups of years between 1860 and 1986. The sigma PAH (16 PAH) concentrations in herbage ranged between 110 and 6900 micrograms kg-1 dry weight, with fluoranthene, pyrene, benzofluoranthenes (b + j + k), chrysene and triphenylene consistently the most abundant. Benz[a]anthracene, benzo[ghi]perylene, benzo[a]pyrene, benzo[e]pyrene and indeno(1,2,3-cd)pyrene were also all important constituents. PAH concentrations in wheat grain ranged from 4 to 46 micrograms sigma PAH kg-1; the mixture of individual compounds was similar to that in herbage. Correcting for yield differences these corresponded to 37-1500 and 2.4-8.8 micrograms sigma PAH m-2 for herbage and wheat grain respectively. The lowest values were found in the most recent samples (1980s) and the highest for samples collected in 1879-81. Generally, there was a decline in the PAH burden of the vegetation with time. The temporal trends of PAHs in the samples are discussed in the context of possible sources of PAHs. Various lines of evidence indicate that the PAH concentrations in vegetation are an indication of atmospheric deposition directly onto the above-ground plant portions, and that uptake and translocation of soil-bound PAHs is of minor importance.

Animal Feed↗
PubMed2002

Phenylphenalenone-related compounds: chemotaxonomic markers of the haemodoraceae from Xiphidium caeruleum.

Phytochemical analysis of Xiphidium caeruleum, a neotropical member of the family Haemodoraceae, resulted in the isolation and identification of a variety of phenylphenalenone-related compounds. The structures of four new phenylbenzoisochromenones (3, 6, 7, 10), a new phenylbenzoisoquinolinone (4), and two new oxabenzochrysenones (11, 12) were elucidated using MS and NMR spectroscopic techniques. In addition, five new glucosides (14-18) were identified, among them four allophanyl glucosides (15-18), representing a novel type of 6'-substituted glucosidic natural product. On the basis of the common occurrence of these 12 new and four known structures (2, 5, 9, 13), hypothetical biosynthetic relationships are discussed. The natural product distribution of other genera of the Haemodoraceae is used as the basis to elaborate biogeographic characteristics of this plant family.

Benzene Derivatives↗
PubMed1999

Toxicity evaluation of organic sediment extracts resolved by size exclusion chromatography using rainbow trout hepatocytes.

The (geno)toxicity of sediment dichloromethane extracts and fractions obtained by size exclusion chromatography were evaluated to investigate effects based on size fractionation. In this study, three sediments were selected according to their incremental contamination in PAHs and in PCBs: Hamilton harbour, Toronto bay and lake St. Clair sediments. Heavy metals, total sulfur and elemental sulfur (S8) were also determined in the (un)fractionated sediment extracts. The liver cells were exposed to concentrations of sediment extracts and fractionated samples for 24 h at 15 degrees C, afterwhich cell viability, cytochrome P4501A1 activity, available free Zn, DNA damage and oxidative stress were determined. The results showed that the sediment extracts contained high levels of sulfur most of which was found in the low molecular weight (LMW) region, i.e., the 2000-50 atomic mass unit (amu) fraction. Elemental sulfur (S8) accounted for 14-41% of extractable sulfur and were found to elute in the post-column volume (PCV) fraction despite its molecular weight of 256 amu. Heavy metals were found mainly in the HMW (i.e. the > 2000 amu) fraction and LMW fractions and very few or none were observed in the PCV fractions. In sediment extracts, sublethal effects were present principally by the HMW and LMW fractions suggesting that some chemicals were also associated with high molecular weight compounds of extractable organic matter. Less toxicity or effect was sometimes found in the extract indicating an antagonistic effect of the contaminants. We found that cell viability and genotoxicity evaluations could be performed on the unfractionated extracts while EROD, available Zn and oxidative stress measurements should be performed on the LMW fractions because of possible antagonist or shielding effects. Considering the cytotoxic responses, the best toxicity ranking in respect to contaminant levels in sediment extract was obtained with the LMW and PCV fractions which accounted for most of the toxic responses in the chromatographic fractions. Moreover, the shielding effect could be explained, in part, by the association of LMW contaminants to large macromolecules.

Animals↗
PubMed2003

Convergent total syntheses of gambierol and 16-epi-gambierol and their biological activities.

The convergent total syntheses of gambierol (1) and 16-epi-gambierol (2) have been achieved. The ABC and FGH ring segments 4 and 5 were prepared from known compounds 6 and 13, respectively, by linear manners. The fragments prepared were connected by our own synthetic strategy including the intramolecular allylation of alpha-acetoxy ether followed by ring-closing metathesis to furnish the octacyclic ether 3. The diiodoalkene 45, prepared from 3, was converted to the Z-iodoalkene 50 via a novel and stereoselective hydrogenolysis followed by deprotection. Construction of the triene side chain was performed by the modified Stille coupling of 50 with the Z-vinylic stannane 41 to afford 1. The similar transformations were carried out on the epimeric octacycle 34 to give 2, which showed no toxicity against mice at the concentration of 14 mg/kg.

Animals↗
PubMed1977

Genetically mediated induction of drug-metabolizing enzymes associated with congenital defects in the mouse.

Various polycyclic aromatic compounds induce certain monooxygenase activities, including aryl hydrocarbon (benzo[a]pyrene) hydroxylase (EC 1.14.14.2), and cytochrome P1-450 in the liver and many nonhepatic tissues of the mouse. This induction process is controlled by the Ah locus. Genetic differences that have been shown in the past to be associated with the Ah locus include an increased susceptibility to chemical carcinogenesis, mutagenicity in vitro, and drug toxicity--manifested as hepatic necrosis, aplastic anemia, or shortened survival time. Pregnant mice received a single injection of 3-methylcholanthrene or 7,12-dimethylbenz[a] anthracene between day 5 and day 13 of gestation, and the uterine contents were examined on day 18. Striking increases were observed in the incidence of MC-1 and DMBA-induced resorptions and congenital malformations in the aromatic hydrocarbon "responsive" C57BL/6N inbred strain, and of DMBA-induced resorptions in the "responsive" C3H/HeN and BALB/cAnN strains--when compared with the similarly treated genetically "nonresponsive" AKR/N strain. These data suggest but do not prove that an association exists between the Ah locus and developmental toxicity, i.e., teratogenesis. Although numerous teratogenic differences among inbred mouse strains have previously reported, this study is unique in that the genetic differences in teratogenicity observed were predicted in advance on the basis of known differences among these strains in polycyclic hydrocarbon metabolism regulated by the Ah locus.

9,10-Dimethyl-1,2-benzanthracene↗
PubMed1997

Three-dimensional quantitative structure-activity relationship of melatonin receptor ligands: a comparative molecular field analysis study.

A three-dimensional quantitative structure-activity relationship using the comparative molecular field analysis (CoMFA) paradigm applied to 57 melatonin receptor ligands belonging to diverse structural families was performed. The compounds studied which have been synthesized previously and reported to be active at chicken brain melatonin receptors were divided into a training set of 48 molecules and a test set of 9 molecules. As most of these compounds have a highly flexible ethylamido side chain, the alignments were based on the most sterically constrained molecule which contains a tricyclic phenalene structure. This tricyclic compound can adopt an axial and an equatorial conformation. Two different molecular superpositions representing possible positioning within the receptor site have been suggested previously. CoMFA was tentatively used to discriminate between alternate hypothetical biologically active conformation and between possible positionings. The best 3D quantitative structure-activity relationship model found yields significant cross-validated, conventional, and predictive r2 values equal to 0.798, 0.967, and 0.76, respectively, along with an average absolute error of prediction of 0.25 log units. These results suggest that the active conformation of the most flexible molecules including melatonin is in a folded form if we consider the spatial position of the ethylamido side chain relative to the aromatic ring.

Animals↗
PubMed1986

Polyaromatic hydrocarbon profile of a mineral oil (JBO-P) by gas chromatography.

The present investigation was aimed at identifying the compound(s) responsible for the carcinogenic activity of a variety of jute batching oil (known as non-FDA variety, pre-FDA variety, or JBO-P), a crude petroleum distillate substantially used in jute industries. This was initially performed by isolating from JBO-P a polyaromatic hydrocarbon (PAH) fraction containing compounds of more than three rings. This fraction was then analysed for its PAH profile by gas chromatography and individual components identified by comparing its flame ionisation detector (FID) signal with those obtained from reference PAHs. The results revealed that PAHs of more than three rings, reported to be a recognised class of chemical carcinogens, were present in the JBO-P sample at the level of 3300 mg/kg of oil (0.33%, w/w); benzo(a)pyrene and dibenz(a,h)anthracene, known to be highly potent carcinogens, constituted 129 mg/kg (0.0129%, w/w) and 29 mg/kg (0.0029%, w/w) of the total oil, respectively; and except for a few signals, the PAH profile of JBO-P was found to be somewhat similar to that reported for a sample of carcinogenic used engine oil.

Chromatography, Gas↗